Stereoselective formation of alpha-quaternary stereocenters in the Mannich reaction.
Condensation of alpha,alpha-disubstituted lithium enolates derived from bicyclic thioglycolate lactams with benzenesulfonyl imines affords Mannich addition products with excellent diastereoselectivity. Cleavage of the auxiliary under hydrolytic or reducing conditions affords beta-amino acids and alcohols, respectively.
Department of Chemistry, McGill University, 801 Sherbrooke St. W., Montreal, QC, Canada.
Erica A
EA
Tiong
James L
JL
Gleason
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D000605:Amino Alcohols; D007097:Imines; D009942:Organometallic Compounds; D008094:Lithium