Diastereoselective synthesis of psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type dipeptide isosteres by organocopper-mediated anti-S(N)2' reaction

Org Lett. 2002 Apr 4;4(7):1051-4. doi: 10.1021/ol016834j.

Abstract

[reaction: see text] Acyclic psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type dipeptide isosteres were efficiently synthesized. In a key reaction, alpha-alkylation of gamma-mesyloxy-beta-methyl-alpha,beta-unsaturated esters with organocyanocuprates in diethyl ether or tetrahydrofuran preferentially afforded the psi[(E)-CH=CMe]- or psi[(Z)-CH=CMe]-isomer, respectively, via anti-S(N)2' mechanism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Copper*
  • Dipeptides / chemical synthesis
  • Dipeptides / chemistry*
  • Indicators and Reagents
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Dipeptides
  • Indicators and Reagents
  • Organometallic Compounds
  • Copper