Mild rhodium(III)-catalyzed C-H allylation with 4-vinyl-1,3-dioxolan-2-ones: direct and stereoselective synthesis of (E)-allylic alcohols

Org Lett. 2014 Dec 19;16(24):6412-5. doi: 10.1021/ol503229c. Epub 2014 Dec 1.

Abstract

A rhodium(III)-catalyzed C-H direct allylation reaction with 4-vinyl-1,3-dioxolan-2-ones has been developed. The reaction provides a facile and stereoselective access to substituted-(E)-allylic alcohols under mild and redox-neutral reaction conditions. Olefinic C-H activation is applicable, giving multifunctionalized skipped dienes in good yields. Minimal double-bond migration was observed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cyclization
  • Dioxolanes / chemistry*
  • Hydrogen Bonding
  • Molecular Structure
  • Propanols / chemical synthesis*
  • Propanols / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism
  • Vinyl Compounds / chemistry*

Substances

  • Alkenes
  • Dioxolanes
  • Propanols
  • Vinyl Compounds
  • allyl alcohol
  • Rhodium
  • ethylene carbonate