A Catalyst that Plays Multiple Roles: Asymmetric Synthesis of β-Substituted Aspartic Acid Derivatives through a Four-Stage, One-Pot Procedure
- 15 January 2002
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (3) , 387-390
- https://doi.org/10.1021/ol017087t
Abstract
We report a new method for the catalytic, asymmetric synthesis of β-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 α-chloroamines to form the corresponding imines; catalyzed [2 + 2]-cycloaddition to produce intermediate acyl β-lactams; and finally, nucleophilic ring opening to afford optically enriched β-substituted aspartic acids in high enantioselectivity and diastereoselectivity.Keywords
This publication has 5 references indexed in Scilit:
- The First Dendrimer-Based Enantioselective Fluorescent Sensor for the Recognition of Chiral Amino AlcoholsPublished by Wiley ,2000
- Catalytic Enantioselective Cyanosilylation of KetonesJournal of the American Chemical Society, 2000
- Synthesis of Catalytically Active Polymers by Means of ROMP: An Effective Approach toward Polymeric Homogeneously Soluble CatalystsThe Journal of Organic Chemistry, 1999
- Catalytic, Enantioselective Alkylation of α-Imino Esters Using Late Transition Metal Phosphine Complexes as CatalystsJournal of the American Chemical Society, 1998
- Total Synthesis of the Novel, Immunosuppressive Agent (−)-Pateamine A from Mycale sp. Employing a β-Lactam-Based MacrocyclizationJournal of the American Chemical Society, 1998