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Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins.

ABSTRACT: Asymmetric hydrogenation has evolved as one of the most powerful tools to construct stereocenters. However, the asymmetric hydrogenation of unfunctionalized tetrasubstituted acyclic olefins remains the pinnacle of asymmetric synthesis and an unsolved challenge. We report herein the discovery of an iridium catalyst for the first, generally applicable, highly enantio- and diastereoselective hydrogenation of such olefins and the mechanistic insights of the reaction. The power of this chemistry is demonstrated by the successful hydrogenation of a wide variety of electronically and sterically diverse olefins in excellent yield and high enantio- and diastereoselectivity.

SUBMITTER: Bigler R

PROVIDER: S-EPMC7141762 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins.

Bigler Raphael R Mack Kyle A KA Shen Jeff J Tosatti Paolo P Han Chong C Bachmann Stephan S Zhang Haiming H Scalone Michelangelo M Pfaltz Andreas A Denmark Scott E SE Hildbrand Stefan S Gosselin Francis F

Angewandte Chemie (International ed. in English) 20200121 7

Asymmetric hydrogenation has evolved as one of the most powerful tools to construct stereocenters. However, the asymmetric hydrogenation of unfunctionalized tetrasubstituted acyclic olefins remains the pinnacle of asymmetric synthesis and an unsolved challenge. We report herein the discovery of an iridium catalyst for the first, generally applicable, highly enantio- and diastereoselective hydrogenation of such olefins and the mechanistic insights of the reaction. The power of this chemistry is d ...[more]

PMID: 31794118

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