Aminocatalysis
Since our initial studies on the first asymmetric proline-catalysed intermolecular aldol reaction in 2000, we and others have established enamine catalysis as a fundamental concept for the catalytic transformation of carbanion equivalents. These pioneering works laid the foundation for the 2021 Nobel Prize in Chemistry, awarded to Benjamin List and David MacMillan for the development of asymmetric organocatalysis, and helped establish organocatalysis as an independent and mature discipline alongside traditional metal and biocatalysis.
Chiral, low-molecular-weight amines are ideally suited to enhance the inherent electrophilic and α-nucleophilic properties of carbonyls via iminium ion or enamine intermediates, respectively, while creating a chiral environment around the reactive centre. In addition to the classical aldol reaction, our group has developed a wide range of further transformations mediated exclusively by catalytic amounts of primary or secondary amines. We strategically utilize this approach to solve real-world chemical challenges that were previously considered difficult to overcome.
Selected publications
Proline-Catalyzed Direct Asymmetric Aldol Reactions
The Direct Catalytic Asymmetric Three-Component Mannich Reaction
Metal-Free, Organocatalytic Asymmetric Transfer Hydrogenation of α,β-Unsaturated Aldehydes
Proline-catalysed Mannich reactions of acetaldehyde
Catalytic, Asymmetric Transannular Aldolizations: Total Synthesis of (+)-Hirsutene
