Asymmetric transfer hydrogenation of boronic acid pinacol ester (Bpin)-containing acetophenones

Org Biomol Chem. 2022 May 11;20(18):3742-3746. doi: 10.1039/d2ob00569g.

Abstract

A series of Bpin-containing acetophenone derivatives were reduced by asymmetric transfer hydrogenation (ATH), using Noyori-Ikariya catalysts, with formic acid/triethylamine, to alcohols in high ee when the Bpin is in the para- or meta-position. Substrates containing ortho-Bpin groups were reduced in lower ee, with formation of a cyclic boron-containing group. The products were converted to substituted derivatives using Pd-catalysed coupling reactions. The results represent the first examples of ATH of Bpin-containing ketones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones
  • Boronic Acids*
  • Esters*
  • Glycols
  • Hydrogenation
  • Stereoisomerism

Substances

  • Acetophenones
  • Boronic Acids
  • Esters
  • Glycols
  • pinacol