Literature DB >> 19764710

Nitro-Mannich/lactamization cascades for the direct stereoselective synthesis of pyrrolidin-2-ones.

Sophie M-C Pelletier1, Peter C Ray, Darren J Dixon.   

Abstract

An efficient three-component nitro-Mannich/lactamization cascade of methyl 3-nitropropanoate with in situ formed acyclic imines for the direct preparation of pyrrolidinone derivatives has been developed. The reaction is easy to perform, broad in scope, and highly diastereoselective and may be extended to cyclic imines allowing the direct formation of polycyclic pyrrolidinone derivatives.

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Year:  2009        PMID： 19764710     DOI： 10.1021/ol901640v

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

2.  Solid-phase synthesis of N-substituted pyrrolidinone-tethered N-substituted piperidines via Ugi reaction.

Authors:  Zhang Liu; Adel Nefzi
Journal:  J Comb Chem       Date:  2010-07-12

3.  Organocatalytic Asymmetric Synthesis of Functionalized 1,3,5-Triarylpyrrolidin-2-ones via an Aza-Michael/Aldol Domino Reaction.

Authors:  Céline Joie; Kristina Deckers; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2014-03-01       Impact factor: 3.157

4.  One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis.

Authors:  David M Barber; Andrej Duriš; Amber L Thompson; Hitesh J Sanganee; Darren J Dixon
Journal:  ACS Catal       Date:  2014-01-06       Impact factor: 13.084

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

Authors:  Pavol Jakubec; Dane M Cockfield; Madeleine Helliwell; James Raftery; Darren J Dixon
Journal:  Beilstein J Org Chem       Date:  2012-04-16       Impact factor: 2.883

6.  Towards the total synthesis of keramaphidin B.

Authors:  Pavol Jakubec; Alistair J M Farley; Darren J Dixon
Journal:  Beilstein J Org Chem       Date:  2016-05-30       Impact factor: 2.883

Review 7.  Recent advances in the chemistry of imine-based multicomponent reactions (MCRs).

Authors:  Lokman H Choudhury; Tasneem Parvin
Journal:  Tetrahedron       Date:  2011-07-18       Impact factor: 2.457
  7 in total

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