Stereoselective synthesis of chiral 4-(1-chloroalkyl)-beta-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines.
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.
Dekeukeleire
Stijn
S
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium.
D'hooghe
Matthias
M
Törnroos
Karl W
KW
De Kimpe
Norbert
N
D000596:Amino Acids / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D001384:Azetidines; D011759:Pyrrolidines; D047090:beta-Lactams