Dimerization of Glycine Derivatives

Abstract

The bromide (5), prepared by treatment of the glycine derivative (4) with N-bromosuccinimide, reacted with hexabutylditin to give diastereoisomers of the glycine dimer (7), only when moisture was rigorously excluded from the reaction. Otherwise the major products were the diastereoisomers of the ether (11). The structure of the racemic diastereoisomer (11) was determined by X-ray crystallography. Photolysis of mixtures of the glycine derivative (4) and di-t-butyl peroxide gave the alanine derivative (10) in addition to the diastereoisomeric dimers (7).