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

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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.

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

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Publication details

The article was received on 04 Dec 2017, accepted on 31 Dec 2017 and first published on 02 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB02989F
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Asymmetric synthesis of (−)-sedacryptine through a diastereoselective Mannich reaction of N,O-acetals with ketones

    Y. Liu, R. Ma, J. Yan, Z. Zhou and B. Wei, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02989F

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