A general and simple diastereoselective reduction by L-Selectride: efficient synthesis of protected (4S,5S)-dihydroxy amides.
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.
Yin
Bo
B
Department of Chemistry and Biology, Ganan Normal University, Jiangxi, China.
Ye
Dong-Nai
DN
Yu
Kai-Hui
KH
Liu
Liang-Xian
LX
D000577:Amides / Q000138:chemical synthesis*; D001880:Boranes / Q000737:chemistry*; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D001880:Boranes; D010880:Piperidines; C533353:selectride