Regio- and stereoselective copper-catalyzed α,β-protoboration of allenoates: access to Z-β,γ-unsaturated β-boryl esters

Org Biomol Chem. 2022 Apr 20;20(16):3287-3291. doi: 10.1039/d2ob00423b.

Abstract

A highly efficient regio- and stereoselective method for allenoate borylation has been developed. Using CuCl and bis(pinacolato)diboron in methanol, a variety of allenoates underwent β-boration and α-protonation to afford the corresponding Z-β,γ-unsaturated β-boryl esters under mild conditions with up to 81% yields.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Copper*
  • Esters*
  • Methanol
  • Stereoisomerism

Substances

  • Esters
  • Copper
  • Methanol