Asymmetric Mannich-type reactions for the synthesis of aspartic acid derivatives from chiral N-tert-butanesulfinylimino esters.
Addition of ketene acetals to sulfinimines derived from homochiral N-tert-butanesulfinamide using various Lewis acids furnishes derivatives of aspartic acid in diastereomeric ratios up to 97:3. Following an easy removal of the N-tert-butanesulfinyl chiral auxiliary, optical active beta-amino esters are obtained.
Jacobsen
Mikkel F
MF
Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.
Skrydstrup
Troels
T
D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004952:Esters / Q000737:chemistry*; D007202:Indicators and Reagents; D007659:Ketones; D009682:Magnetic Resonance Spectroscopy; D008352:Mannich Bases / Q000737:chemistry*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
D004952:Esters; D007202:Indicators and Reagents; D007659:Ketones; D008352:Mannich Bases; C481933:N-tert-butanesulfinylimino ester; D013452:Sulfonium Compounds; D001224:Aspartic Acid