A catalyst that plays multiple roles: asymmetric synthesis of beta-substituted aspartic acid derivatives through a four-stage, one-pot procedure

Travis Dudding; Ahmed M Hafez; Andrew E Taggi; Ty R Wagerle; Thomas Lectka

doi:10.1021/ol017087t

A catalyst that plays multiple roles: asymmetric synthesis of beta-substituted aspartic acid derivatives through a four-stage, one-pot procedure

Org Lett. 2002 Feb 7;4(3):387-90. doi: 10.1021/ol017087t.

Authors

Travis Dudding¹, Ahmed M Hafez, Andrew E Taggi, Ty R Wagerle, Thomas Lectka

Affiliation

¹ Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, MD 21218, USA.

PMID: 11820886
DOI: 10.1021/ol017087t

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Aspartic Acid / analogs & derivatives*
Aspartic Acid / chemical synthesis
Catalysis

Substances

Aspartic Acid