A THERMODYNAMIC PREFERENCE OF CHIRAL CIS-GAMMA,DELTA-EPIMINO-(E)-ALPHA,BETA-UNSATURATED ESTERS OVER OTHER STEREOISOMERS - SYNTHETICALLY USEFUL PD(0)-CATALYZED EQUILIBRATED REACTIONS OF AZIRIDINES BEARING AN ALPHA,BETA-UNSATURATED ESTER GROUP

摘要

A practical synthesis of chiral N-arylsulfonyl-cis-gamma,delta-epimino-(E)-alpha,beta- enoates, key intermediates for the synthesis of (E)-alkene dipeptide isosteres via Pd(O)-catalyzed equilibrated reactions, has been successfully achieved by exposing N-arylsulfonyl-gamma,delta-epimino-alpha,beta-unsaturated esters to a catalytic amount of Pd(PPh(3))(4) in THF at 0 similar to 20 degrees C. Copyright (C) 1996 Elsevier Science Ltd. [References: 23]