title: Diastereoselective Synthesis of 1-Deoxygalactonojirimycin, 1-Deoxyaltronojirimycin, and N-Boc-(2S,3S)-3-Hydroxypipecolic Acid via Proline Catalyzed α-Aminoxylation of Aldehydes.
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.
authors: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, India 208016.
authors: Shibin
authors: S
authors: Chacko
authors: Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, India 208016.
authors: Ramesh
authors: R
authors: Ramapanicker
mesh_terms: D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D008968:Molecular Conformation; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; C553837:L-altro-1-deoxynojirimycin; C000603412:N-Boc-(2S,3S)-3-hydroxypipecolic Acid; D010875:Pipecolic Acids; D017485:1-Deoxynojirimycin; D011392:Proline; C090092:migalastat