Asymmetric synthesis of (−)-sedacryptine through a diastereoselective Mannich reaction of N,O-acetals with ketones†,10.1039/C7OB02989F

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Asymmetric synthesis of (−)-sedacryptine through a diastereoselective Mannich reaction of N,O-acetals with ketones†

Yi-Wen Liu,Rui-Jun Ma,Jia-Hang Yan,Zhu Zhou,Bang-Guo Wei

Organic & Biomolecular Chemistry Pub Date : 01/02/2018 00:00:00 , DOI:10.1039/C7OB02989F

Abstract

An efficient diastereoselective approach to access the 3-hydroxy-2,6-disubstituted piperidine scaffold 1 has been developed through the Mannich process involving N,O-acetal (2S,3R)-6 and ketones in excellent yield with high diastereoselectivity (dr > 99 : 1). In addition, the utility of this convenient one-pot process is demonstrated by the asymmetric synthesis of (−)-sedacryptine 3.