Homogeneous Catalysis
Our group focuses on the development of new catalysis concepts within the areas of organocatalysis, transition metal catalysis, and, to some extent, biocatalysis. Since 1999, the List-group concentrates on enantioselective organocatalysis as a fundamental approach complementing biocatalysis and transition metal catalysis. We have a profound interest in developing “new reactions”, designing and identifying new principles for the development of organocatalysts, expanding the scope of already developed catalysts such as proline, using organocatalysis in the synthesis of natural products and pharmaceuticals, and also investigating the mechanism by which organocatalysts activate their substrates. Furthermore, in 2005 our group has first conceptualized another approach to asymmetric catalysis, namely asymmetric counteranion directed catalysis (ACDC). This idea has not only progressed within the department but also at other institutions around the globe into a general strategy for asymmetric synthesis applied in organocatalysis as well as in transition metal catalysis and Lewis acid catalysis.
Prof. Dr. Benjamin List
- since 2012
- Managing Director at the Max-Planck-Institut für Kohlenforschung
- since 2005
- Director at the Max-Planck-Institut für Kohlenforschung
- since 2005
- Scientific member of the Max-Planck-Society
- since 2004
- Honorary Professor at the University of Cologne
- 2003–2005
- Group Leader at the Max-Planck-Institut für Kohlenforschung
- 1999–2003
- Assistant Professor (Tenure Track), Scripps Research Institute, La Jolla, USA
- 1997–1998
- Post-Doc, Scripps Research Institute, La Jolla, USA
- 1997
- PhD, University Frankfurt (J. Mulzer)
- 1993
- Chemistry Diplom, Free University Berlin
- 1968
- Born in Frankfurt/Germany
- 2013
- Mukaiyama Award 2013
- 2013
- Horst-Pracejus-Preis
- 2012
- Otto-Bayer-Preis
- 2012
- Novartis Chemistry Lectureship Award
- 2011
- Boehringer-Ingelheim Lectureship, Harvard University, USA
- 2011
- ERC Advanced Grant
- 2009
- Thomson Reuters Citation Laureate
- 2009
- Organic Reactions Lectureship, USA
- 2009
- Boehringer-Ingelheim Lectureship, Canada
- 2008
- Visiting Professor at Sungkyunkwan University, Korea
- 2007
- AstraZeneca Award in Organic Chemistry
- 2007
- 2007 OBC-Lecture Award
- 2007
- Award of the Fonds der Chemischen Industrie
- 2006
- 100 Masterminds of Tomorrow, Germany
- 2006
- JSPS Fellowship Award, Japan
- 2006
- Wiechert Lectureship, FU-Berlin, Germany
- 2005
- Novartis Young Investigator Award
- 2005
- AstraZeneca European Lecturer 2005
- 2005
- Visiting Professor at Gakushuin University, Tokyo/Japan
- 2005
- The Society of Synthetic Chemistry, Japan: 2005 Lectureship Award
- 2004
- Lieseberg-Price of the University of Heidelberg
- 2004
- "Lecturer's Award" of the Fonds der Chemischen Industrie
- 2004
- Degussa Prize for Chirality in Chemistry
- 2003
- Carl-Duisberg-Memorial Award of the German Chemical Society
- 2000
- Synthesis-Synlett Journal Award
- 1997
- Feodor-Lynen Fellowship of the Alexander von Humboldt Foundation
- 1994
- NaFöG-Award from the City of Berlin
-
University of Cologne
Lectures "Organocatalysis"
- since 2011
- Regional Editor "Synlett", Thieme
- since 2010
- Member of the Editorial Advisory Panel "Nature Communications"
- since 2008
- Member of the Editorial Advisory Board "Beilstein Journal of Organic Chemistry"
- since 2005
- Editor "Synfacts", Thieme
- 2005-2011
- Programme Coordinator of the DFG Priority Programme SPP1179
- 2008-2009
- Editor: "Asymmetric Organocatalysis", Topics in Current Chemistry
- 2006
- Editor: "Organocatalysis", Chemical Reviews
- 2004
- Co-Editor, Special Edition: "Organocatalysis", Adv. Synth. Cat
- 2013
- 146.) Ji Hye Kim, Ilija Čorić, Sreekumar Vellalath, and Benjamin List*:The Catalytic Asymmetric Acetalization.145.) Ilija Čorić, Ji Hye Kim, Tjøstil Vlaar, Mahendra Patil, Walter Thiel and Benjamin List*:Brønsted Acid Catalyzed Asymmetric SN2-Type O-Alkylations.144.) Ilija Čorić, Sreekumar Vellalath, Steffen Müller, Xu Cheng and Benjamin List*:Developing Catalytic Asymmetric Acetalizations.143.) Shikha Gandhi and Benjamin List*:Catalytic Asymmetric Three-Component Synthesis of Homoallylic Amines.142.) Joyram Guin, Georgy Varseev and Benjamin List*:Catalytic Asymmetric Protonation of Silyl Ketene Imines.141.) Manuel Mahlau and Benjamin List*:Asymmetric Counteranion-Directed Catalysis: Concept, Definition, and Applications.
- 2012
- 140.) Manuel Mahlau, Pilar García-García and Benjamin List*:Asymmetric Counteranion-Directed Catalytic Hosomi–Sakurai Reaction.139.) Manuel Mahlau and Benjamin List*:Asymmetric Synthesis II (Ed. M. Christmann, S. Bräse)Wiley-VCH, Weinheim, 2012, 79-84.138.) Ji-Woong Lee and Benjamin List*:Deracemization of α-Aryl Hydrocoumarins via Catalytic Asymmetric Protonation of Ketene Dithioacetals.137.) Keiji Maruoka, Benjamin List, Hisashi Yamamoto and Liu-Zhu Gong:Organocatalysis: a web collection.136.) Benjamin List, Sai-Hu Liao, Seiji Shirakawa, Keiji Maruoka, Liu-Zhu Gong and Wen-Jing Xiao:(Ed. Kuiling Ding, Li-Xin Dai)Organic Chemistry - Breakthroughs and PerspectivesThe Proline-Catalyzed Mannich Reaction and the Advent of Enamine Catalysis135.) Nicolas Demoulin, Olga Lifchits and Benjamin List*:Organocatalytic Asymmetric α-Benzoyloxylation of α-Branched Aldehydes and Enals. A Useful Approach to Oxygenated Quaternary Stereocenters.134.) Saihu Liao and Benjamin List*:Asymmetric Counteranion-Directed Iron Catalysis: A Highly Enantioselective Sulfoxidation.133.) Benjamin List:Organocatalysis.132.) Manuel Mahlau and Benjamin List*:Asymmetric Counteranion-Directed Catalysis (ACDC): A Remarkably General Approach to Enantioselective Synthesis.131.) Joyram Guin, Constantinos Rabalakos and Benjamin List*:Highly Enantioselective Hetero-Diels-Alder Reaction of 1,3-Bis(silyloxy)-1,3-dienes with Aldehydes Catalyzed by Chiral Disulfonimide.Activation of H2O2 by Chiral Confined Brønsted Acids: A Highly Enantioselective Catalytic Sulfoxidation.Catalytic Asymmetric Epoxidation of 2-Cyclopentenones.
128.) Ilija Čorić and Benjamin List*:Asymmetric Spiroacetalization Catalysed by Confined Brønsted Acids.127.) Benjamin List (Vol. Ed.)Asymmetric Organocatalysis 1: Lewis Base and Acid Catalysts. - 2011
- 126.) Steffen Müller, Matthew J. Webber and Benjamin List*:
The Catalytic Asymmetric Fischer Indolization.
J. Am. Chem. Soc., 2011, 133, 18534-18537.
125.) Gaoxi Jiang, Rajkumar Halder, Yewen Fang and Benjamin List*:
A Highly Enantioselective Overman Rearrangement through Asymmetric Counteranion-Directed Palladium Catalysis.
Angew. Chem. Int. Ed. 2011, 50, 9752-9755.124.) Olga Lifchits, Nicolas Demoulin, Benjamin List*:
Direct Asymmetric α Benzoyloxylation of Cyclic Ketones.
Angew. Chem. Int. Ed. 2011, 50, 9680-9683.123.) Gaoxi Jiang and Benjamin List*:
Direct Asymmetric α-Allylation of Aldehydes with Simple Allylic Alcohols Enabled by the Concerted Action of Three Different Catalysts.
Angew. Chem. Int. Ed. 2011, 50, 9471-9474.122.) Gaoxi Jiang and Benjamin List*:
Enantioselective hydrovinylation via asymmetric counteranion-directed ruthenium catalysis.
121.) Benjamin List: Cluster Preface:
Challenges of Proline-Based Aminocatalysis.
Synlett 2011, 4, 462-463.
120.) Gaoxi Jiang and Benjamin List*:
Palladium/Brønsted Acid Catalyzed α-Allylation of Aldehydes with Allylic Alcohols.
Adv. Synth. Catal., DOI10.1002.
119.) Anna Lee, Anna Michrowska, Sarah Sulzer-Mosse and Benjamin List:
The Catalytic Asymmetric Knoevenagel Condensation.
Angew. Chem. Int. Ed. 2011, 50, 1707-1710.118.) Lars Ratjen, Pilar García-García, Frank Lay, Michael Edmund Beck, Benjamin List*: Disulfonimide-Catalyzed Asymmetric Vinylogous and Bisvinylogous Mukaiyama Aldol Reactions.
Angew. Chem. Int. Ed. 2011, 50, 754-758. - 2010
117.) Vijay Wakchaure, Marcello Nicoletti, Lars Ratjen, Benjamin List*:
Towards a Practical Brønsted Acid Catalyzed and Hantzsch Ester Mediated Asymmetric Reductive Amination of Ketones with Benzylamine.
Synlett 2010, 18, 2708-2710.116.) Martin Klussmann, Lars Ratjen, Sebastian Hoffmann, Vijay Wakchaure, Richard Goddard, Benjamin List*:
Synthesis of TRIP and Analysis of Phosphate Salt Impurities.
Synlett 2010, 14, 2189-2192.115.) Dominique Anna Bock, Christian W. Lehmann, Benjamin List*:
Crystal structures of proline-derived enamines.
PNAS 2010, 107 (48), 20636-20641.114.) Sreekumar Vellalath, Ilija Coric, Benjamin List*:
N-Phosphinyl Phosphoramide - A Chiral Brønsted Acid Motif for the Direct Asymmetric N,O-Acetalization of Aldehydes.
Angew. Chem. Int. Ed. 2010, 49, 9749-9752.113.) Ilija Coric, Steffen Müller, Benjamin List*:
Kinetic Resolution of Homoaldols via Catalytic Asymmetric Transacetalization.
J. Am. Chem. Soc. 2010, 132, 17370-17373.112.) Zhang, Y., F. Lay, P. García-García, Benjamin List and E.Y.-X. Chen:
High-Speed Living Polymerization of Polar Vinyl Monomers by Self-Healing Silylium Catalysts.
Chemistry - A European Journal 2010, 16 (34), 10462-10473.111.) Lars Ratjen, Steffen Müller, Benjamin List*:
ACDC - not just for heavy metal fans.
Nachrichten aus der Chemie 2010, 58, 640-646.110.) Steffen Müller, Benjamin List*:
Catalytic asymmetric 6π-electrocyclization: accessing highly substituted optically active 2-pyrazolines via diastereoselective alkylations.
Synthesis 2010, 2171-2178.109.) Olga Lifchits, Corinna M. Reisinger, Benjamin List*:
Catalytic Asymmetric Epoxidation of α-Branched Enals.
J. Am. Chem. Soc. 2010, 132, 10227-10229.108.) Vijay N. Wakchaure, Jian Zhou, Sebastian Hoffmann, Benjamin List*:
Catalytic Asymmetric Reductive Amination of α-Branched Ketones.
Angew. Chem. Int. Ed. 2010, 49, 4612-4614.107.) Ilija Coric, Sreekumar Vellalath, Benjamin List*:
Catalytic Asymmetric Transacetalization.
J. Am. Chem. Soc. 2010, 132, 8536-8537. [Erratum J. Am. Chem. Soc. 2010, 132, 12155.]106.) Vijay N. Wakchaure, Benjamin List*:
A New Structural Motif for Bifunctional Brønsted Acid/Base Organocatalysis.
Angew. Chem. Int. Ed. 2010, 49, 4136-4139.105.) Kristina Zumbansen, Arno Döhring, Benjamin List*:
Morpholinium Trifluoroacetate Catalyzed Aldol Condensation of Acetone with both Aromatic and Aliphatic Aldehydes.
Adv. Synth. Catal. 2010, 352, 1135-1138.104.) Benjamin List:
Enough Organocatalysis? (Ed.)
Top. Curr. Chem. 2010, 291, Asymmetric Organocatalysis, ix-x.103.) Daniela Kampen, Corinna M. Reisinger and Benjamin List*:
Chiral Brønsted Acids for Asymmetric Organocatalysis.
Top. Curr. Chem. 2010, 291, 395-456.102.) Benjamin List*:
Emil Knoevenagel and the Roots of Aminocatalysis.
Angew. Chem. Int. Ed. 2010, 49, 1730-1734.101.) Saihu Liao and Benjamin List*:
Asymmetric Counteranion-Directed Transition-Metal Catalysis: Enantioselective Epoxidation of Alkenes with Manganese(III) Salen Phosphate Complexes.
Angew. Chem. Int. Ed. 2010, 49, 628-631.- 2009
100.) Steffen Müller and Benjamin List*:
A Catalytic Asymmetric 6 π Electrocyclization: Enantioselective Synthesis of 2-Pyrazolines.
Angew. Chem. Int. Ed. 2009, 48, 9975-9978.99.) Anna Michrowska and Benjamin List*:
Concise synthesis of ricciocarpin A and discovery of a more potent analogue.
Nature Chem. 2009, 1, 225-228.98.) Pilar Garcia Garcia, Frank Lay, Patricia Garcia Garcia, Constantinos Rabalakos and Benjamin List*:
A Powerful Chiral Counteranion Motif for Asymmetric Catalysis.
Angew. Chem. Int. Ed. 2009, 48, 4363-4366.97.) Rubén Manzano, Lidia Ozores, Andreas Job, Lars Rodefeld and Benjamin List*:
Catalytic Synthesis of (E)-α,β -Unsaturated Esters from Aldehydes and 1,1-Diethoxyethylene.
Beilstein J. Org. Chem. 2009, 5, doi:10.3762/bjoc.5.3.96.) Carley Chandler, Patrizia Galzerano, Anna Michrowska and Benjamin List*:
The Proline-Catalyzed Double Mannich Reaction of Acetaldehyde with N-Boc Imines.
Angew. Chem. Int. Ed. 2009, 48, 1978-1980.95.) Wolfgang Schrader, Peni Purwa Handayani, Jian Zhou and Benjamin List*:
Characterization of Key Intermediates in a Complex Organocatalytic Cascade Reaction Using Mass Spectrometry.
Angew. Chem. Int. Ed. 2009, 48, 1463-1466.94.) Jung Woon Yang, Subhas Chandra Pan and Benjamin List*:
Synthesis of tert-Butyl (1S,2S)-2-methyl-3-oxo-1-phenylpropylcarbamate by Asymmetric Mannich Reaction.
Org. Synth. 2009, 86, 11-17.- 2008
93.) Xu Cheng, Sreekumar Vellalath, Richard Goddard and Benjamin List*:
Direct Catalytic Asymmetric Synthesis of Cyclic Aminals from Aldehydes.
J. Am. Chem. Soc. 2008, 130, 15786-15787.92.) Nolwenn J. A. Martin, Xu Cheng and Benjamin List*:
Organocatalytic Asymmetric Transferhydrogenation of β-Nitroacrylates: Accessing β2-Amino Acids.
J. Am. Chem. Soc. 2008, 130, 13862-13863.91.) Corinna M. Reisinger, Xingwang Wang and Benjamin List*:
Catalytic Asymmetric Hydroperoxidation of α,β-Unsaturated Ketones: An Approach to Enantiopure Peroxyhemiketals, Epoxides, and Aldols.
Angew. Chem. Int. Ed. 2008, 47, 8112-8115.90.) Jian Zhou, Vijay Wakchaure, Philip Kraft and Benjamin List*:
Primary-Amine-Catalyzed Enantioselective Intramolecular Aldolizations.
Angew. Chem. Int. Ed. 2008, 47, 7656-7658.89.) Gareth Adair, Santanu Mukherjee and Benjamin List*:
TRIP-A Powerful Brønsted Acid Catalyst for Asymmetric Synthesis.
Aldrichimica Acta 2008, 41, 31-39.88.) Xu Cheng, Richard Goddard, Gernoth Buth and Benjamin List*:
Direct Catalytic Asymmetric Three-Component Kabachnik-Fields Reaction.
Angew. Chem. Int. Ed. 2008, 47, 5079-5081.87.) Patricia García-García, Arnaud Ladépêche, Rajkumar Halder and Benjamin List*:
Catalytic Asymmetric Michael Reactions of Acetaldehyde.
Angew. Chem. Int. Ed. 2008, 47, 4719-4721.86.) Carley L. Chandler and Benjamin List*:
Catalytic Asymmetric Transannular Aldolizations: Total Synthesis of (+)-Hirsutene.
J. Am. Chem. Soc. 2008, 130, 6737-6739.85.) Xingwang Wang, Corinna M. Reisinger and Benjamin List*:
Catalytic Asymmetric Epoxidation of Cyclic Enones.
J. Am. Chem. Soc. 2008, 130, 6070-6071.84.) Subhas Chandra Pan and Benjamin List*:
Catalytic Three-Component Ugi Reaction.
Angew. Chem. Int. Ed. 2008, 47, 3622-3625.83.) Daniela Kampen, Arnaud Ladépêche, Gerrit Claßen and Benjamin List*:
Brønsted Acid-Catalyzed Three-Component Hosomi-Sakurai Reactions.
Adv. Synth. Catal. 2008, 350, 962-966.82.) Jung Woon Yang, Carley Chandler, Michael Stadler, Daniela Kampen and Benjamin List*:
Proline-catalysed Mannich reaction of acetaldehyde.
Nature 2008, 452, 453-455.81.) Michael Stadler and Benjamin List*:
Heck Reactions of Crotonaldehyde.
Synlett 2008, 597-599.80.) Subhas Chandra Pan and Benjamin List*:
The Catalytic Acylcyanation of Imines.
Chem. Asian J. 2008, 3, 430-437.79.) Xingwang Wang and Benjamin List*:
Asymmetric Counteranion-Directed Catalysis for the Epoxidation of Enals.
Angew. Chem. Int. Ed. 2008, 47, 1119-1122.- 2007
78.) Subhas C. Pan and Benjamin List*:
New Concepts for Organocatalysis
In Ernst Schering Research Foundation Workshop,
M. T. Reetz, B. List, S. Jaroch and H. Weinmann (Eds.), Springer Berlin Heidelberg, 2007, 2, 1-4377.) Benjamin List*:
Introduction: Organocatalysis.
Chem. Rev. 2007, 107, 5413-5415.76.) Santanu Mukherjee, Jung Woon Yang, Sebastian Hoffmann and Benjamin List*:
Asymmetric Enamine Catalysis.
Chem. Rev. 2007, 107, 5471-5569.75.) Santanu Mukherjee and Benjamin List*:
Chiral Counteranions in Asymmetric Transition-Metal Catalysis: Highly Enantioselective Pd/Brønsted Acid-Catalyzed Direct α-Allylation of Aldehydes.
J. Am. Chem. Soc. 2007, 129, 11336-11337.74.) Jung Woon Yang, Michael Stadler and Benjamin List*:
Practical Proline-Catalyzed Asymmetric Mannich Reaction of Aldehydes with N-Boc-imines.
Nat. Protocols 2007, 2(8), 1937-1942.73.) Jian Zhou and Benjamin List*:
Synthesis of trans-3-Substituted Cyclohexylamines via Brønsted Acid Catalyzed and substrate-Mediated Triple Organocatalytic Cascade Reaction.
Synlett 2007, 2037-2040.72.) Nolwenn J. A. Martin, Lidia Ozores and Benjamin List*:
Organocatalytic Asymmetric Transfer Hydrogenation of Nitroolefins.
J. Am. Chem. Soc. 2007, 129, 8976-8977.71.) Jian Zhou and Benjamin List*:
Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines.
J. Am. Chem. Soc. 2007, 129, 7498-7499.70.) Benjamin List:
Biocatalysis and Organocatalysis: Asymmetric Synthesis Inspired by Nature. In Asymmertic Synthesis:
The Essentials, Christmann, M. and Bräse, S., Ed. Wiley-VCH: Weinhein, Germany, 2007, 161-165.69.) Santanu Mukherjee and Benjamin List*:
Radical Catalysis (News and Views).
Nature 2007, 447, 152-153.68.) Xiaoguang Li and Benjamin List*:
Catalytic Asymmetric Hydrogenation of Aldehydes.
Chem. Commun. 2007, 17, 1739-1741.67.) Subhas Chandra Pan and Benjamin List*:
Catalytic One-Pot, Three-Component Acyl-Strecker Reaction.
Synlett 2007, 318-320.66.) Subhas Chandra Pan and Benjamin List*:
Catalytic Asymmetric Three-Component Acyl-Strecker Reaction.
Org. Lett. 2007, 9, 1149-1151.65.) Subhas Chandra Pan, Jian Zhou, and Benjamin List*:
Catalytic Asymmetric Acylcyanation of Imines.
Angew. Chem. Int. Ed. 2007, 46, 612-614.
64.) Jung Woon Yang, Michael Stadler, and Benjamin List*:
Proline-Catalyzed Mannich Reaction of Aldehydes with N-Boc-Imines.
Angew. Chem. Int. Ed. 2007, 46, 609-611.- 2006
63.) Subhas Chandra Pan, Jian Zhou and Benjamin List*:
Catalytic Acylcyanation of Imines with Acetylcyanide.
Synlett 2006, 3275-3276.62.) Jung Woon Yang* and Benjamin List*:
Catalytic Asymmetric Transfer Hydrogenation of α-Ketoesters with Hantzsch Esters.
Org. Lett. 2006, 8, 5653-5655.61.) Benjamin List* and Jung Woon Yang:
The Organic Approach to Asymmetric Catalysis (Perspective).
Science 2006, 313 (5793), 1584-1586.60.) Nolwenn J. A. Martin and Benjamin List*:
Highly Enantioselective Transfer Hydrogenation of α,β-Unsaturated Ketones.
J. Am. Chem. Soc. 2006, 128, 13368-13369.59.) Daniela Kampen and Benjamin List*:
Efficient Brønsted Acid Catalyzed Hosomi–Sakurai Reaction of Acetals.
Synlett 2006, 2589-2592.58.) Sebastian Hoffmann, Marcello Nicoletti, and Benjamin List*:
Catalytic Asymmetric Reductive Amination of Aldehydes via Dynamic Kinetic Resolution.
J. Am. Chem. Soc. 2006, 128, 13074-13075.57.) Sonja Mayer and Benjamin List*:
Asymmetric Counteranion-Directed Catalysis.
Angew. Chem. Int. Ed. 2006, 45, 4193-4195.56.) Aiping Fu, Benjamin List* and Walter Thiel*:
Density Functional Study of the Enantioselectivity in the 2-Methylproline-Catalyzed α-Alkylation of Aldehydes.
J. Org. Chem. 2006, 71, 320-326.55.) Benjamin List*:
The Ying and Yang of Asymmetric Aminocatalysis.
Chem. Comm. 2006, 819-824.54.) Jayasree Seayad, Abdul Majeed Seayad, and Benjamin List*:
Catalytic Asymmetric Pictet-Spengler Reaction.
J. Am. Chem. Soc. 2006, 128, 1086-1087.53.) Benjamin List*, Arno Doehring, Maria T. Hechavarria Fonseca, Andreas Job and Ramon Rios Torres:
A Practical, efficient, and atom economic alternative to the Wittig and Horner–Wadsworth-Emmons reactions for the synthesis of (E)-α,β-unsaturated esters from aldehydes.
Tetrahedron 2006, 62, 476-482.- 2005
52.) Jayasree Seayad and Benjamin List:
Catalytic Asymmetric Multi-Component Reactions.
In Multi-Component Reactions, Zhu, J. and Bienayme, H., Eds.Wiley-VCH: Weinhein, Germany, 2005.51.) Sebastian Hoffmann, Abdul Majeed Seayad, and Benjamin List*:
A Powerful Brønsted Acid Catalyst for the Organocatalytic Asymmetric Transfer Hydrogenation of Imines.
Angew. Chem. Int. Ed. 2005, 44, 7424-7427.50.) Jung Woon Yang, Maria H. Fonseca, and Benjamin List*:
Catalytic Asymmetric Reductive Michael Cyclization.
J. Am. Chem. Soc. 2005, 127, 15036-15037.49.) Benjamin List*, Arno Doehring, Maria T. Hechavarria Fonseca, Kathrin Wobser, Hendrik van Thienen, Ramon Rios Torres, Pedro Llamas Galilea:
Practical Synthesis of (E)-α,β-Unsaturated Esters from Aldehydes.
Adv. Synth. Catal. 2005, 347, 1558 – 1560.48.) Jayasree Seayad and Benjamin List*:
Asymmetric Organocatalysis.
Org. Biomol. Chem. 2005, 3, 719-724.47.) Jung Woon Yang, Maria H. Fonseca, Nicola Vignola and Benjamin List*:
Metal-Free, Organocatalytic Asymmetric Transfer Hydrogenation of α,β-Unsaturated Aldehydes.
Angew. Chem. Int. Ed. 2005, 44, 108-110.- 2004
46.) Jung Woon Yang, Maria T. Hechavarria Fonseca and Benjamin List*:
A Metal-Free Transfer Hydrogenation: Organocatalytic Conjugate Reduction of α,β-Unsaturated Aldehydes.
Angew. Chem. Int. Ed. 2004, 43, 6660-6662.45.) Benjamin List:
Organokatalyse: Eine neue und breit anwendbare Synthesemethode
In: Jahrb. - Max-Planck-Ges., Vandenhoeck & Ruprecht: Göttingen, 2004, S. 353-356.44.) Benjamin List:
Organocatalysis: A Complementary Catalysis Strategy Advances Organic Synthesis.
Adv. Synth. Catal. 2004, 346, 1021.43.) Benjamin List:
Amine-Catalyzed Aldol Reactions.
In Modern Aldol Reactions, Vol. 1, Mahrwald, R., Ed. Wiley-VCH: Weinhein, Germany, 2004, 161-200.42.) Benjamin List*:
Enamine Catalysis is a Powerful Strategy for the Catalytic Generation and Use of Carbanion Equivalents.
Acc. Chem. Res. 2004, 37, 548-557.41.) K. N. Houk and Benjamin List:
Asymmetric Organocatalysis.
Acc. Chem. Res. 2004, 37, 487-487.40.) Maria T. Hechavarria Fonseca and Benjamin List*:
Catalytic Asymmetric Intramolecular Michael Reaction of Aldehydes.
Angew. Chem. Int. Ed. 2004, 43, 3958-3960.39.) Maria T. Hechavarria Fonseca and Benjamin List*:
Combinatorial Chemistry and High-Throughput-Screening for the Discovery of Organocatalysts.
Curr. Opin. Chem. Biol. 2004, 8, 319-326.38.) Benjamin List*, Linh Hoang, and Harry J. Martin:
New Mechanistic Studies on the Proline-Catalyzed Aldol Reaction.
Proc. Natl. Acad. Sci. 2004, 101, 5839-5842.37.) Nicola Vignola, Benjamin List*:
Catalytic Asymmetric Intramolecular α-Alkylation of Aldehydes.
J. Am. Chem. Soc. 2004, 126, 450-451.- 2003
36.) Peter Pojarliev, William T. Biller, Harry J. Martin, Benjamin List*:
Highly Enantioselective Synthesis of 1,2-Amino Alcohol Derivatives via Proline-Catalyzed Mannich Reaction.
Synlett 2003, 1903-1905.35.) Harry J. Martin, Benjamin List*:
Mining Sequence Space for Asymmetric Aminocatalysis: N-Terminal Prolyl-Peptides Efficiently Catalyze Enantioselective Aldol and Michael Reactions.
Synlett 2003, 1901-1902.34.) Chandrakala Pidathala, Linh Hoang, Nicola Vignola, and Benjamin List*:
Direct Catalytic Asymmetric Enolexo-Aldolizations.
Angew. Chem. Int. Ed. 2003, 42, 2785-2788.33.) S. Bahmanyar, K. N. Houk*, Harry J. Martin, and Benjamin List*:
Quantum Mechanical Predictions of the Stereoselectivities of Proline-Catalyzed Asymmetric Intermolecular Aldol Reactions.
J. Am. Chem. Soc. 2003, 125, 2475-2479.32.) Linh Hoang, S. Bahmanyar, K. N. Houk, and Benjamin List*:
Kinetic and Stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of Proline-Catalyzed Intra- and Intermolecular Aldol Reactions.
J. Am. Chem. Soc. 2003, 125, 16-17.- 2002
31.) Benjamin List*:
Proline-Catalyzed Asymmetric Reactions.
Tetrahedron 2002, 58, 5573-5590.30.) Benjamin List*:
Direct Catalytic Asymmetric α-Amination of Aldehydes.
J. Am. Chem. Soc. 2002, 124, 5656-5657.29.) Benjamin List*, Peter Pojarliev, William T. Biller, and Harry J. Martin:
The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction:
Scope, Optimization, and Application to the Highly Enantioselective Synthesis of 1,2-Amino Alcohols.
J. Am. Chem. Soc. 2002, 124, 827-833.- 2001
28.) Dorothy S. Worrall, Jonathan E. McDunn, Benjamin List, Donna Reichart, Andrea Hevener, Thomas Gustafson, Carlos F. Barbas III, Richard A. Lerner* and Jerrold M. Olefsky*:
Synthesis of an Organoinsulin Molecule that can be Activated by Antibody Catalysis.
Proc. Natl. Acad. Sci. 2001, 98, 13514-13518.27.) Cecilia Subauste*, Benjamin List, Xiaojun Guan, Klaus M. Hahn, Richard A. Lerner, Norton B. Gilula:
A Catalytic Antibody Produces Fluorescent Tracers of Gap Junction Communication in Living Cells.
J. Biol. Chem. 2001, 276, 49164-49168.26.) Benjamin List*:
Asymmetric Aminocatalysis.
Synlett 2001, 1675-1686.25.) Benjamin List* and Chris Castello:
A Novel Proline-Catalyzed Three-Component Reaction of Ketones, Aldehydes, and Meldrum’s Acid.
Synlett 2001, 1687-1689.24.) Benjamin List*, Peter Pojarliev, and Harry J. Martin:
Efficient Proline-Catalyzed Michael-Additions of Unmodified Ketones to Nitroolefins.
Org. Lett. 2001, 3, 2423-2425.23.) Benjamin List*, Peter Pojarliev, and Chris Castello:
Proline-Catalyzed Asymmetric Aldol Reactions between Ketones and α-Unsubstituted Aldehydes.
Org. Lett. 2001, 3, 573-575.- 2000
22.) Benjamin List*:
The Direct Catalytic Asymmetric Three-Component Mannich Reaction.
J. Am. Chem. Soc. 2000, 122, 9336-9337.21.) Wolfgang Notz and Benjamin List*:
Catalytic Asymmetric Synthesis of anti-1,2-Diols.
J. Am. Chem. Soc. 2000, 122, 7386-7387.20.) Carlos F. Barbas III*, Christoph Reader, David J. Segal, Benjamin List, and James M. Turner:
From Catalytic Asymmetric Synthesis to the Transcriptional Regulation of Genes: In Vivo and In Vitro evolution of Proteins.
Advances in Protein Chemistry 2000, 55, 317-366.19.) James Turner, Tommy Bui, Richard A. Lerner*, Carlos F. Barbas*, and Benjamin List*:
An Efficient Benchtop System for Multigram-Scale Kinetic Resolutions Using Aldolase Antibodies.
Chem. Eur. J. 2000, 6, 2772-2774.18.) Christoph Rader and Benjamin List*:
Catalytic Antibodies as Magic Bullets.
Chem. Eur. J. 2000, 6, 2091-2095.17.) Benjamin List*, Richard. A. Lerner, and Carlos F. Barbas III:
Proline-Catalyzed Direct Asymmetric Aldol Reactions.
J. Am. Chem. Soc. 2000, 122, 2395-2396.16.) Amelie Karlstrom, Guofu Zhong, Christoph Rader, Nicholas A. Larsen, Andreas Heine, Roberta Fuller, Benjamin List, Fujie Tanaka, Ian A. Wilson, Carlos F. Barbas III*, and Richard A. Lerner*:
Using Antibody Catalysis to Study the Outcome of Multiple Evolutionary Trials of a Chemical Task.
Proc. Natl. Acad. Sci. 2000, 97, 3878-3883.- 1994-1999
15.) Benjamin List, Doron Shabat, Guofu Zhong, James M. Turner, Tony Li, Tommy Bui, James Anderson, Richard. A. Lerner* and Carlos F. Barbas III*:
A Catalytic Enantioselective Route to Hydroxy-Substituted Quaternary Carbon Centers: Resolution of Tertiary Aldols with a Catalytic Antibody.
J. Am. Chem. Soc. 1999, 121, 7283-7291.14.) Doron Shabat, Christoph Rader, Benjamin List, Richard. A. Lerner*, and Carlos F. Barbas III*:
Multiple Event Activation of a Generic Prodrug Trigger by Antibody Catalysis.
Proc. Natl. Acad. Sci. 1999, 96, 6925-6930.13.) Benjamin List, Richard. A. Lerner*, and Carlos F. Barbas III*:
Enantioselective Aldol-Cyclodehydrations Catalyzed by Antibody 38C2.
Org. Lett. 1999, 1, 59-62.12.) Doron Shabat, Benjamin List, Richard A. Lerner* and Carlos F. Barbas III*:
A Short Enantioselective Synthesis of 1-Deoxy-L-Xylulose by Antibody Catalysis.
Tetrahedron Lett. 1999, 40, 1437-40.11.) Benjamin List, Carlos F. Barbas III* and Richard. A. Lerner*:
Aldol Sensors for the Rapid Generation of Tunable Fluorescence by Antibody Catalysis.
Proc. Natl. Acad. Sci. 1998, 15351-55.10.) Carlos F. Barbas III and Benjamin List:
Alchemy, Enzymes, and the Blind-Watchmaker.
Nature Biotechnology 1998, 16, 423-24.9 .) Benjamin List, Doron Shabat, Carlos F. Barbas III* and Richard A. Lerner*:
Enantioselective Total Synthesis of Some Brevicomins Using Aldolase Antibody 38C2.
Chem. Eur. J. 1998, 881-885.8.) Guofu Zhong, Doron Shabat, Benjamin List, James Anderson, Subash C. Sinha, Richard A. Lerner* and Carlos F. Barbas III*:
Catalytic Enantioselective Retro-Aldol Reactions: Kinetic Resolution of β-Hydroxyketones with Aldolase Antibodies.
Angew. Chem., Int. Ed. 1998, 37, 2481-84.7.) Torsten Hoffmann, Guofu Zhong, Benjamin List, Doron Shabat, James Anderson, Svetlana Gramatikova, Richard A. Lerner* and Carlos F. Barbas III*:
Aldolase Antibodies of Remarkable Scope.
J. Am. Chem. Soc. 1998, 120, 2768-79.6.) Carlos F. Barbas III*, Andreas Heine, Guofu Zhong, Torsten Hoffmann, Svetlana Gramatikova, Robert Bjoernstedt, Benjamin List, James Anderson, Enrico A. Stura, Ian Wilson* and Richard A. Lerner*:
Immune vs. Natural Selection: Antibody Aldolases with Enzymic Rates but Broader Scope.
Science 1997, 278, 2085-2092.5.) Johann Mulzer*, Jan W. Bats, Benjamin List, Till Opatz and Dirk Trauner:
The Phenanthrenone Approach to Opium Alkaloids: Formal Total Synthesis of Morphine by Sigmatropic Rearrangement.
Synlett 1997, 441-44.4.) Johann Mulzer*, Benjamin List and Jan W. Bats:
Stereocontrolled Synthesis of a Nonracemic Vitamin B12 A-B Semicorrin.
J. Am. Chem. Soc. 1997, 119, 5512-18.3.) Johann Mulzer*, Harry J. Martin and Benjamin List:
Three Component, One-Pot Synthesis of α,β-Unsaturated Ketones.
Tetrahedron Lett. 1996, 37, 9177-78.2.) Johann Mulzer* and Benjamin List:
[2,3]-Wittig Rearrangement of (Trimethylsilyl)methyl Allyl Ethers.
Tetrahedron Lett. 1996, 37, 2403-04.1.) Johann Mulzer* and Benjamin List:
Highly Stereoselective Synthesis of Tetrasubstituted Alkenes via [2,3]-Wittig Rearrangement.
Tetrahedron Lett. 1994, 35, 9021-24.
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Ben List receives "Novartis Chemistry Lectureship Award 2012/2013"
The Novartis Chemistry Lectureship is awarded to scientists in recognition of outstanding contributions to organic and computational chemistry, including applications to biology. It is intended to enhancing the exposure of Novartis' chemical community to cutting edge chemistry. The lectures are attended by medicinal and process chemists from Novartis, and are also open to scientists from other companies and universities. During the next two years, the lectureship will bring Prof. List to all main research sites of Novartis including Basel/CH, Cambridge/US, Emeryville/US, La Jolla/US, Horsham/UK, Shanghai/PRC, and Singapore.
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University of Cologne
Lectures "Organocatalysis"
Research Topics
- Organocatalysis
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Organocatalysis
Our research aims towards the invention of new strategies for the development of "perfect chemical reactions" that combine quantitative yields and high atom economy, while not requiring toxic solvents, protecting groups, heating, cooling, or inert gas atmosphere. We approach this ultimate goal by using selective catalysis based on small organic molecules. In recent years it has been demonstrated that these organocatalysts can be as efficient and selective as the more commonly used metal-based catalysts, resulting in an “explosive” research activity in this new and exciting area of Organocatalysis.
- Aminocatalysis
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Aminocatalysis
We explore small-molecule amines as asymmetric catalysts for carbonyl transformations. “Asymmetric Aminocatalysis” functions by activating carbonyl compounds as iminium ions and enamines using a catalytic amount of an amine. Our strategy complements existing catalytic methods based on chiral acids and bases that typically involve metals. After our studies on the first asymmetric proline-catalyzed intermolecular aldol reaction in 2000, we realized that enamine catalysis has the potential to be a general strategy for the catalytic utilization of carbanion equivalents. Since then we have discovered several other transformations that can be catalyzed by primary or secondary amines. Currently our research aims towards the synthesis and identification of new catalyst structures to tackle further exciting and challenging problems and to discover new amine-catalyzed transformations.
- Brønsted Acid Catalysis
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Brønsted Acid Catalysis
The number of reactions that can be catalyzed by Brønsted acids may well exceed that of those that cannot. In light of this, Brønsted acid catalysis has become a focus of our research. We are constantly looking for useful transformations that can be catalyzed with Brønsted acids. For example, we have developed a Brønsted acid catalyzed Hosomi-Sakurai reaction (2006) and the catalytic 3-component Ugi reaction (2008). Besides this, the asymmetric catalysis of such reactions is a major goal of our work. Thereby the design of new active and selective catalyst motifs comes along with mechanistic studies leading to an understanding of the reaction, ultimately allowing for the rational design of improved catalysts.
- Organic Lewis Acid Catalysis
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Organic Lewis Acid Catalysis
The field of Lewis acid catalysis is so far strongly dominated by (transition) metal chemistry. To provide the purely organic counterparts to these traditional catalytic systems we are dedicated to the synthesis and identification of organic Lewis acids. In 2009 we found that our newly synthesized chiral disulfonimides are not only excellent Brønsted acids, but turn into strong Lewis acids upon silylation. These chiral Lewis acids can easily activate simple aldehydes at catalyst loadings as low as 0.001 mol% and catalyze enantioselective Mukaiyama aldol reactions with high enantioselectivities. Very recently we were able to extend this concept to the asymmetric vinylogous Mukaiyama aldol reaction as well as to almost unprecedented enantioselective bisvinylogous Mukaiyama aldol reactions. Considering the many Lewis acid catalyzed reactions, these examples are clearly just the beginning of this exciting area of organic Lewis acid catalysis. Studies towards a deep understanding of the mode of action as well as the elaboration of new organic Lewis acid catalyzed transformations are the subject of intense research in our group.
- Asymmetric Couteranion Directed Catalysis (ACDC)
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Asymmetric Couteranion Directed Catalysis (ACDC)
Most reactions proceed via charged intermediates and/or transition states. This allows to manipulate the course of a reaction and consequently also its stereochemical outcome by careful choice of a chiral counterion. In asymmetric phase transfer catalysis this concept is well established by using e.g. chiral quaternary ammonium cations. However, the anionic counterpart to this methodology, the use of chiral anions to influence the stereochemical outcome of reactions proceeding via cationic intermediates has been elusive for a long time. In 2006 we disclosed that the combination of a chiral phosphate anion and an achiral amine is a powerful catalytic system for the highly enantioselective transfer hydrogenation of enals in which the asymmetric induction is solely provided by the chiral counteranion. During the last years we have extended this concept to other organocatalytic as well as metal catalyzed transformations, focusing on innovative reactions and potentially new chiral counteranions.
- Synthesis of Natural Products and Biologically Active Compounds
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Synthesis of Natural Products and Biologically Active Compounds
The ultimate goal of method development in organic synthesis is to provide useful and reliable tools for the synthesis of complex molecules such as natural products or biologically relevant compounds and to lead to a better understanding of the underlying principles. The value of a new method is often judged by the number of possible applications and the gain of knowledge it comes along with. In our group we are tackling chemical problems of asymmetric bond construction that are basically unsolved yet. Consequently a successfully developed new method should provide access to useful building blocks that can be used to easily ensemble complex molecules. Therefore the synthesis of natural products and pharmaceuticals is an important element of our research, not only to evaluate the potential of a new method, but also as a stimulus and source of inspiration towards new exciting discoveries.
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Baum, Florian
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