Related Experiment Video
Updated: Jan 2, 2026
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins
Raphael Bigler1, Kyle A Mack2, Jeff Shen2
1Pharmaceutical Division, Small Molecules Technical Development, Department of Process Chemistry and Catalysis, F. Hoffmann-La Roche Ltd, 4070, Basel, Switzerland.
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.
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