Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles

Beilstein Journal of Organic Chemistry

Madeleine Helliwell¹  James Raftery¹  Dane M. Cockfield¹  Darren J. Dixon²  Pavol Jakubec² 

[1] School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK;The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK;

关键词: cascade;    imine;    Michael addition;    nitro-Mannich;    organocatalysis;    piperidine alkaloids;   

DOI  :  10.3762/bjoc.8.64

来源: DOAJ

【 摘 要 】

A versatile nitro-Mannich/lactamisation cascade for the direct stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles has been developed. A highly enantioenriched substituted 5-nitropiperidin-2-one was synthesised in a four component one-pot reaction combining an enantioselective organocatalytic Michael addition with the diastereoselective nitro-Mannich/lactamisation cascade. Protodenitration and chemoselective reductive manipulation of the heterocycles was used to install contiguous and fully substituted stereocentres in the synthesis of substituted piperidines.

【 授权许可】

Unknown