title: A general and simple diastereoselective reduction by L-Selectride: efficient synthesis of protected (4S,5S)-dihydroxy amides.
abstract: A general approach to (4S,5S)-4-benzyloxy-5-hydroxy-N-(4-methoxybenzyl) amides 10 based on a diastereoselective reduction of (5S,6RS)-6-alkyl-5-benzyloxy-6-hydroxy-2-piperidinones 6 and their tautomeric ring-opened keto amides 7 is described. The reduction with L-Selectride at -20 degrees C to room temperature afforded the products 10 in excellent yields and moderate to high syn-diastereoselectivities.
authors.affiliation: Department of Chemistry and Biology, Ganan Normal University, Jiangxi, China.
authors.forename: Bo
authors.initials: B
authors.lastname: Yin
authors.forename: Dong-Nai
authors.initials: DN
authors.lastname: Ye
authors.forename: Kai-Hui
authors.initials: KH
authors.lastname: Yu
authors.forename: Liang-Xian
authors.initials: LX
authors.lastname: Liu
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D001880:Boranes / Q000737:chemistry*; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D001880:Boranes; D010880:Piperidines; C533353:selectride