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Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins. | LitMetric

Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins.

Angew Chem Int Ed Engl

Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA, 94080, USA.

Published: February 2020

AI Article Synopsis

  • Asymmetric hydrogenation has become a key method for creating stereocenters, but the hydrogenation of unfunctionalized tetrasubstituted acyclic olefins is still a major challenge.
  • Researchers have discovered a new iridium catalyst that enables highly selective hydrogenation of these challenging olefins.
  • The new method shows outstanding effectiveness across various olefin types, achieving high yields and selectivity in the reactions.

Article 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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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7141762PMC
http://dx.doi.org/10.1002/anie.201912640DOI Listing

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