Synthesis of chiral (alpha,alpha-difluoroalkyl)phosphonate analogues of (lyso)phosphatidic acid via hydrolytic kinetic resolution

Org Lett. 2002 Nov 14;4(23):4021-4. doi: 10.1021/ol026684s.

Abstract

The hydrolytic kinetic resolution of 1,1-difluoro-3,4-epoxy-butylphosphonate using a chiral salen-Co complex was employed as a key step to obtain enantiomeric diols in 99% ee as key intermediates. The enantiomerically homogeneous (alpha,alpha-difluoroalkyl)phosphonates were obtained after selective esterification and deprotection of the corresponding phosphonates. These compounds are novel phosphatase-resistant analogues of lysophosphatidic acid and phosphatidic acid. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrolysis
  • Kinetics
  • Lysophospholipids / chemical synthesis
  • Lysophospholipids / chemistry*
  • Organophosphonates*
  • Phosphatidic Acids / chemical synthesis
  • Phosphatidic Acids / chemistry*
  • Stereoisomerism

Substances

  • Lysophospholipids
  • Organophosphonates
  • Phosphatidic Acids