Alternative synthesis of P-chiral phosphonite-borane complexes: application to the synthesis of phostone-phostone dimers

J Org Chem. 2013 Jul 19;78(14):6858-67. doi: 10.1021/jo400864s. Epub 2013 Jun 26.

Abstract

An improved strategy for the synthesis of P-chiral gluco- and manno-phosphonite-borane complexes is described on the basis of the addition of diethyl phosphonite-borane to a glucal-derived aldehyde, followed by a cyclization coupled with an ethyl/methyl exchange. This direct P(III) strategy facilitates the obtention of various P-chiral phosphonite-boranes, of which further coupling reactions are described leading to the selective synthesis of two phostone dimers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boranes / chemistry*
  • Dimerization
  • Molecular Structure
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry*

Substances

  • Boranes
  • Organophosphorus Compounds