Asymmetric synthesis of new chiral beta-amino acid derivatives by Mannich-type reactions of chiral N-sulfinyl imidates with N-tosyl aldimines.
New chiral beta-(sulfonylamino)sulfinylimidates are synthesized in high overall yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of chiral N-tert-butanesulfinyl imidates with N-tosyl aldimines. Deprotection of the beta-(sulfonylamino)sulfinylimidates gave access to enantiopure imidate hydrochlorides in high yields, as useful intermediates for an easy transformation to new chiral beta-sulfonylamino amides upon simple heating in chloroform. Hydrolysis of the imidate hydrochlorides afforded the corresponding chiral beta-sulfonylamino esters with >98% ee as new chiral beta-amino acid derivatives.
Colpaert
Filip
F
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Mangelinckx
Sven
S
De Kimpe
Norbert
N
D000596:Amino Acids / Q000737:chemistry*; D006868:Hydrolysis; D007094:Imides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D007094:Imides; D007097:Imines