An enantioselective synthesis of (+)-polyoxamic acid via phase-transfer catalytic conjugate addition and asymmetric dihydroxylation

J Org Chem. 2011 Jan 21;76(2):740-3. doi: 10.1021/jo102272h. Epub 2010 Dec 30.

Abstract

A new enantioselective synthetic method of (+)-polyoxamic acid is reported. (+)-Polyoxamic acid could be obtained in 7 steps with 46% overall yield from diphenylmethyl-glycineimine tert-butyl ester via an enantioselective phase-transfer conjugate addition (99% yield, 96% ee) and an asymmetric dihydroxylation (98% yield, 94% de) as the key reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Catalysis
  • Hydroxylation
  • Molecular Structure
  • Stereoisomerism
  • Sugar Acids / chemical synthesis*
  • Sugar Acids / chemistry*

Substances

  • Amino Acids
  • Sugar Acids
  • polyoxamic acid