Diastereoselective synthesis of fluorinated, seven-membered beta-amino acid derivatives via ring-closing metathesis

Org Lett. 2003 Jul 10;5(14):2523-6. doi: 10.1021/ol034827k.

Abstract

[reaction: see text] Cis and trans seven-membered gamma,gamma-difluorinated beta-amino acid derivatives (III) have been prepared with a sequence that starts with imidoyl halides (I), which are condensed with suitable ester enolates to give intermediates (II). These, in turn, can be cyclized by means of a ring-closing olefin metathesis reaction and the product stereoselectively reduced to yield compounds (III) in good overall yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Fluorine / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Fluorine