A catalyst that plays multiple roles: asymmetric synthesis of beta-substituted aspartic acid derivatives through a four-stage, one-pot procedure
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Updated: Aug 11, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Travis Dudding1, Ahmed M Hafez, Andrew E Taggi
1Department of Chemistry, Johns Hopkins University, 3400 North Charles St., Baltimore, MD 21218, USA.
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.
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