Stereoselective Synthesis of Chiral 4-(1-Chloroalkyl)-β-Lactams Starting from Amino Acids and Their Transformation into Functionalized Chiral Azetidines and Pyrrolidines

Abstract

Chiral short-chain alpha-chloroaldehydes were prepared starting from enantiomerically pure amino acids in a three-step approach, thus providing a practical synthetic alternative for known organocatalytic alpha-chlorination procedures. The latter aldehydes proved to be useful starting materials for the stereoselective Staudinger synthesis of (3S,4S)-4-[(1S)-1-chloroalkyl]azetidin-2-ones in high diastereomeric ratios and good overall yields, which were used as chiral building blocks for the preparation of a number of azetidines and pyrrolidines.