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Diastereoselective Synthesis of 1-Deoxygalactonojirimycin, 1-Deoxyaltronojirimycin, and N-Boc-(2S,3S)-3-Hydroxypipecolic Acid via Proline Catalyzed α-Aminoxylation of Aldehydes

Author:
Chacko, Shibin, Ramapanicker, Ramesh
Source:
Journal of organic chemistry 2015 v.80 no.9 pp. 4776-4782
ISSN:
1520-6904
Subject:
aldehydes, catalysts, catalytic activity, chemical reactions, chemical structure, diastereoselective synthesis, organic chemistry, proline
Abstract:
An efficient synthesis of deoxygalactonojirimycin and deoxyaltronojirimycin through the use of proline catalyzed asymmetric α-aminoxylation of a higher homologue of Garner’s aldehyde, derived from l-aspartic acid, is reported. The method is also used for a highly diastereoselective synthesis of the N-Boc derivative of (2S,3S)-3-hydroxypipecolic acid. The configuration of the proline catalyst used for the asymmetric aminoxylation step ultimately controls the absolute configuration of three adjacent stereogenic centers in the final products.
Agid:
5505386