A catalyst that plays multiple roles: asymmetric synthesis of beta-substituted aspartic acid derivatives through a four-stage, one-pot procedure.
We report a new method for the catalytic, asymmetric synthesis of beta-substituted aspartic acid derivatives in which the nucleophilic catalyst serves up to four discrete roles in a one-pot procedure: catalytic dehydrohalogenation of acid chlorides to form ketenes; catalytic dehydrohalogenation of alpha-chloroamines to form the corresponding imines; catalyzed [2 + 2]-cycloaddition to produce intermediate acyl beta-lactams; and finally, nucleophilic ring opening to afford optically enriched beta-substituted aspartic acids in high enantioselectivity and diastereoselectivity.
Dudding
Travis
T
Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, MD 21218, USA.
Hafez
Ahmed M
AM
Taggi
Andrew E
AE
Wagerle
Ty R
TR
Lectka
Thomas
T
D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002384:Catalysis
D001224:Aspartic Acid