A stereoselective synthesis of anti-gamma,delta-alkynyl- and -alkenyl-beta-hydroxy-alpha-amino esters from tin(II) enolates of glycinate

Chem Commun (Camb). 2003 Oct 21:(20):2550-1. doi: 10.1039/b306291k.

Abstract

Condensations between the tin(II) enolate 11 of ethyl N-tosylglycinate and conjugated ynals 12 and ynones 14 are highly diastereoselective, in favour of the anti-isomers 13 and 15; similar reactions of enals and enones 17 show lower but still useful levels of anti-stereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Alkynes / chemistry
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Esters / chemistry*
  • Glycine / analogs & derivatives*
  • Glycine / chemistry*
  • Organotin Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Alkynes
  • Amino Acids
  • Esters
  • Organotin Compounds
  • Glycine