Literature DB >> 18763784

Cyclic imine nitro-Mannich/lactamization cascades: a direct stereoselective synthesis of multicyclic piperidinone derivatives.

Pavol Jakubec1, Madeleine Helliwell, Darren J Dixon.   

Abstract

An efficient nitro-Mannich/lactamization cascade of gamma-nitro esters with cyclic imines for the preparation of architecturally complex multicyclic piperidinone ring-containing structures has been developed. The reaction is broad in scope and stereoselective and may be coupled to an enantioselective nitroolefin Michael addition reaction as part of a highly enantio- and diastereoselective multicomponent process.

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Year:  2008        PMID： 18763784     DOI： 10.1021/ol801666w

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


  7 in total

1.  Organocatalytic asymmetric assembly reactions for the syntheses of carbohydrate derivatives by intermolecular Michael-Henry reactions.

Authors:  Hisatoshi Uehara; Ritsuo Imashiro; Gloria Hernández-Torres; Carlos F Barbas
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-16       Impact factor: 11.205

2.  Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines.

Authors:  Kaikai Wang; Yanli Li; Wei Zhang; Rongxiang Chen; Xueji Ma; Mingyue Wang; Nan Zhou
Journal:  Molecules       Date:  2022-05-10       Impact factor: 4.927

3.  Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams.

Authors:  Douglas C Behenna; Yiyang Liu; Taiga Yurino; Jimin Kim; David E White; Scott C Virgil; Brian M Stoltz
Journal:  Nat Chem       Date:  2011-12-18       Impact factor: 24.427

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.  Solvent-Free C-3 Coupling of Azaindoles with Cyclic Imines.

Authors:  Khadija Belasri; Ferenc Fülöp; István Szatmári
Journal:  Molecules       Date:  2019-10-04       Impact factor: 4.411

6.  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

7.  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
  7 in total

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