Asymmetric Mannich-type reactions for the synthesis of aspartic acid derivatives from chiral N-tert-butanesulfinylimino esters

Mikkel F Jacobsen; Troels Skrydstrup

doi:10.1021/jo034436j

Asymmetric Mannich-type reactions for the synthesis of aspartic acid derivatives from chiral N-tert-butanesulfinylimino esters

J Org Chem. 2003 Sep 5;68(18):7112-4. doi: 10.1021/jo034436j.

Authors

Mikkel F Jacobsen¹, Troels Skrydstrup

Affiliation

¹ Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark.

PMID: 12946161
DOI: 10.1021/jo034436j

Abstract

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.

Publication types

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

MeSH terms

Aspartic Acid / analogs & derivatives*
Aspartic Acid / chemical synthesis
Esters / chemistry*
Indicators and Reagents
Ketones
Magnetic Resonance Spectroscopy
Mannich Bases / chemistry*
Stereoisomerism
Sulfonium Compounds / chemistry*

Substances

Esters
Indicators and Reagents
Ketones
Mannich Bases
N-tert-butanesulfinylimino ester
Sulfonium Compounds
Aspartic Acid