Manganese(III)-promoted highly stereoselective phosphorylation of acyclic tertiary enamides to synthesize E-selective β-phosphoryl enamides

Org Biomol Chem. 2022 Jul 20;20(28):5566-5574. doi: 10.1039/d2ob00980c.

Abstract

A concise manganese(III)-promoted stereoselective β-phosphorylation of acyclic tertiary enamides and diverse H-phosphine oxides was achieved. This reaction proceeds with absolute E-selectivity in contrast to Z-selectivity obtained in other previous works and affords various E-selective β-phosphorylated tertiary enamides in high efficiency. To the best of our knowledge, this is the first case of E-selective β-phosphorylation of tertiary enamides through C-H functionalization. In addition, the method features broad substrate scope, good functional group compatibility and efficient scale-up.

Publication types

  • Case Reports
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides*
  • Humans
  • Manganese*
  • Molecular Structure
  • Phosphorylation
  • Stereoisomerism

Substances

  • Amides
  • Manganese