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Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins
Author(s) -
Bigler Raphael,
Mack Kyle A.,
Shen Jeff,
Tosatti Paolo,
Han Chong,
Bachmann Stephan,
Zhang Haiming,
Scalone Michelangelo,
Pfaltz Andreas,
Denmark Scott E.,
Hildbrand Stefan,
Gosselin Francis
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201912640
Subject(s) - asymmetric hydrogenation , stereocenter , chemistry , steric effects , iridium , enantioselective synthesis , yield (engineering) , organic chemistry , catalysis , noyori asymmetric hydrogenation , frustrated lewis pair , combinatorial chemistry , lewis acids and bases , materials science , metallurgy
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.