Kempf D J, Wang X C, Spanton S G
Pharmaceutical Products Division, Abbott Laboratories, Abbott Park, IL.
Int J Pept Protein Res. 1991 Sep;38(3):237-41.
A new stereocontrolled synthesis of the psi[CH = CH] dipeptide isostere is described. They key step of the sequence relies on the stereospecific alpha-alkylation of delta-amino-gamma-mesyloxy-alpha,beta-unsaturated esters. The broad availability of nucleophilic alpha-side chains by this method allows the preparation of a wide variety of psi[CH = CH] isosteres with predictable stereochemistry.
