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04/04/18

Unprecedented Reactivity in Organocatalysis: Prof. Benjamin List and Research Team Publish Asymmetric Activation of Olefins in “Science”

Unprecedented Reactivity in Organocatalysis: Prof. Benjamin List and Research Team Publish Asymmetric Activation of Olefins in “Science”

Olefins are one of the most fundamental compound classes in chemistry and are often obtained directly from crude oil. The use of this ubiquitous functionality to introduce molecular complexity is therefore highly sought-after. Though Nature uses biologically enzymes, chemists generally consider transition metal catalysis as the preferred strategy for asymmetric olefin activation. While organocatalysis has quickly become one of the pillars of catalysis since its inception in the late 1990s, its use in asymmetric olefin activation has remained out of reach.

In a breakthrough discovery, Prof. Benjamin List, Director at the Max-Planck-Institut für Kohlenforschung, and his research team have overcome this major limitation of modern organocatalysis to achieve an unprecedented asymmetric hydroalkoxylation reaction of simple olefins. The method is operationally simple and can be applied toward the synthesis of biologically active compounds. Prof. List says “The asymmetric activation of unbiased olefins using an organocatalyst has been considered one of the most prominent limitations in our field since its infancy. Inspired by the extraordinary capabilities of enzymes, we are excited to now have designed the technology to activate such non-polar functionalities with a chiral Brønsted acid catalyst. We look forward to exploring the capacity of these catalysts to activate olefins in several other reactions.”
The research team, led by PhD student Nobuya Tsuji, describes their work in “Activation of olefins via asymmetric Brønsted acid catalysis” now published in Science.