Cobalt-Catalyzed Enantioconvergent Hydrogenation of Minimally Functionalized Isomeric Olefins

J Am Chem Soc. 2022 Sep 28;144(38):17359-17364. doi: 10.1021/jacs.2c08525. Epub 2022 Sep 15.

Abstract

Investigation on asymmetric hydrogenation of olefins is of great importance in both pharmaceutical molecule synthesis and chemical industry due to the high demand for enantiopure compounds. The established methods often require geometrically pure olefins. The enantioconvergent reaction provided the possibility to access a single stereoisomer via hydrogenation of E/Z-olefin mixtures; however, a polar functional group next to the carbon-carbon double bond was usually necessary. Here, we reported a cobalt-catalyzed enantioconvergent hydrogenation of readily available minimally functionalized E/Z-olefin mixtures. This strategy shows good functional group tolerance and provides an alternative means to enantioconvergent transformation. The preliminary mechanistic studies indicated that cobalt-catalyzed isomerization was the key to achieve the convergent transformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes* / chemistry
  • Carbon / chemistry
  • Catalysis
  • Cobalt* / chemistry
  • Hydrogenation
  • Isomerism
  • Pharmaceutical Preparations

Substances

  • Alkenes
  • Pharmaceutical Preparations
  • Cobalt
  • Carbon