Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins

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

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)2844-2849
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number7
DOIs
StatePublished - Feb 10 2020

Keywords

  • N,P ligands
  • asymmetric catalysis
  • hydrogenation
  • iridium
  • tetrasubstituted olefins

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins'. Together they form a unique fingerprint.

  • Cite this

    Bigler, R., Mack, K. A., Shen, J., Tosatti, P., Han, C., Bachmann, S., Zhang, H., Scalone, M., Pfaltz, A., Denmark, S. E., Hildbrand, S., & Gosselin, F. (2020). Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins. Angewandte Chemie - International Edition, 59(7), 2844-2849. https://doi.org/10.1002/anie.201912640