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Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins
Authors:Raphael Bigler  Kyle A. Mack  Jeff Shen  Paolo Tosatti  Chong Han  Stephan Bachmann  Haiming Zhang  Michelangelo Scalone  Andreas Pfaltz  Scott E. Denmark  Stefan Hildbrand  Francis Gosselin
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.
Keywords:asymmetric catalysis  hydrogenation  iridium  N,P ligands  tetrasubstituted olefins
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