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

Beilstein Journal of Organic Chemistry
Pavol JakubecDarren J Dixon

Abstract

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.

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Citations

Mar 7, 2013·Chemical Reviews·Adam Noble, James C Anderson
Mar 5, 2016·Organic & Biomolecular Chemistry·Ying-Chieh Wong, Ying-Yeung Yeung
Oct 12, 2013·Chemistry : a European Journal·Ulf Scheffler, Rainer Mahrwald
Jun 28, 2016·Angewandte Chemie·Peter G K ClarkDarren J Dixon
Apr 14, 2015·Angewandte Chemie·Peter G K ClarkDarren J Dixon
Oct 23, 2016·Drug Discovery Today. Technologies·Peter G K ClarkPaul E Brennan
Oct 9, 2012·Journal of the American Chemical Society·Pavol JakubecDarren J Dixon
Jun 25, 2016·Beilstein Journal of Organic Chemistry·Pavol JakubecDarren J Dixon
Jan 16, 2018·Organic & Biomolecular Chemistry·Wannaporn Disadee, Somsak Ruchirawat

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