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