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Chiral Organic Contact Ion Pairs in Metal-Free Catalytic Asymmetric Allylic Substitutions

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journal contribution
posted on 23.03.2011, 00:00 by Magnus Rueping, Uxue Uria, Ming-Yuan Lin, Iuliana Atodiresei
Chiral contact ion-pair catalysis with particular focus on metal-free processes is gaining in interest. As a result, new perspectives are opened, and highly stereoselective transformations, traditionally performed under metal catalysis, can be realized. Herein, we report the development of an unprecedented asymmetric Brønsted acid-catalyzed allylic alkylation. The concept relies on chiral contact ion-pair catalysis, in which the chiral organic counteranion of an allylic carbocation induces high enantioselectivities and allows access to biologically relevant chromenes in good yields and with excellent enantioselection.