Diastereoselective Synthesis of 1-Deoxygalactonojirimycin, 1-Deoxyaltronojirimycin, and N-Boc-(2S,35)-3-Hydroxypipecolic Acid via Pro line Catalyzed alpha-Aminoxylation of Aldehydes

摘要

An efficient synthesis of deoxygalactonojirimycin and deoxyaltronojirimycin through the use of proline catalyzed asymmetric alpha-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 cents in the final products.