Literature DB >> 25278634

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

Céline Joie1, Kristina Deckers1, Dieter Enders1.   

Abstract

The organocatalytic asymmetric synthesis of functionalized 1,3,5-triarylpyrrolidin-2-ones bearing three contiguous stereocenters through an aza-Michael/aldol domino reaction of α-ketoamides with α,β-unsaturated aldehydes is described. The domino products were further derivatized by aldehyde olefination under one-pot conditions. The reaction proceeds with excellent diastereoselectivities (>20:1) and good to excellent enantioselectivities (60-96% ee).

Entities:  

Keywords:  asymmetric synthesis; aza-Michael addition; domino reactions; organocatalysis; pyrrolidin-2-ones

Year:  2014        PMID： 25278634      PMCID： PMC4178285          DOI： 10.1055/s-0033-1340565

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  46 in total

1.  An organocatalytic cascade approach toward polysubstituted quinolines and chiral 1,4-dihydroquinolines-unanticipated effect of N-protecting groups.

Authors:  Xinshuai Zhang; Xixi Song; Hao Li; Shilei Zhang; Xiaobei Chen; Xinhong Yu; Wei Wang
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-13       Impact factor: 15.336

2.  A new approach for an organocatalytic multicomponent domino asymmetric reaction.

Authors:  Armando Carlone; Silvia Cabrera; Mauro Marigo; Karl Anker Jørgensen
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Asymmetric organocatalytic domino Michael/aldol reactions: enantioselective synthesis of chiral cycloheptanones, tetrahydrochromenones, and polyfunctionalized bicyclo[3.2.1]octanes.

Authors:  Magnus Rueping; Alexander Kuenkel; Francisco Tato; Jan W Bats
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Asymmetric organocatalytic four-component quadruple domino reaction initiated by oxa-Michael addition of alcohols to acrolein.

Authors:  Fang-Lin Zhang; Ai-Wen Xu; Yue-Fa Gong; Mo-Hui Wei; Xiang-Liang Yang
Journal:  Chemistry       Date:  2009-07-13       Impact factor: 5.236

5.  Quadruple domino organocatalysis: an asymmetric aza-Michael/Michael/Michael/aldol reaction sequence leading to tetracyclic indole structures with six stereocenters.

Authors:  Dieter Enders; Andreas Greb; Kristina Deckers; Philipp Selig; Carina Merkens
Journal:  Chemistry       Date:  2012-07-02       Impact factor: 5.236

6.  One-pot formation of chiral polysubstituted 3,4-dihydropyrans via a novel organocatalytic domino sequence involving alkynal self-condensation.

Authors:  Li-Jin Dong; Tian-Tian Fan; Chao Wang; Jian Sun
Journal:  Org Lett       Date:  2012-12-21       Impact factor: 6.005

7.  Enantioselective organocatalytic tandem Michael-Aldol reactions: one-pot synthesis of chiral thiochromenes.

Authors:  Wei Wang; Hao Li; Jian Wang; Liansuo Zu
Journal:  J Am Chem Soc       Date:  2006-08-16       Impact factor: 15.419

8.  Highly diastereo- and enantioselective organocatalytic domino Michael/aldol reaction of acyclic 3-halogeno-1,2-diones to α,β-unsaturated aldehydes.

Authors:  Alice Lefranc; Laure Guénée; Alexandre Alexakis
Journal:  Org Lett       Date:  2013-04-22       Impact factor: 6.005

9.  Lessons from nature: biomimetic organocatalytic carbon-carbon bond formations.

Authors:  Dieter Enders; Arun A Narine
Journal:  J Org Chem       Date:  2008-09-09       Impact factor: 4.354

Review 10.  Development of cascade reactions for the concise construction of diverse heterocyclic architectures.

Authors:  Liang-Qiu Lu; Jia-Rong Chen; Wen-Jing Xiao
Journal:  Acc Chem Res       Date:  2012-05-11       Impact factor: 22.384
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  4 in total

1.  An Asymmetric Organocatalytic Quadruple Cascade to Tetraaryl-Substituted 2-Azabicyclo[3.3.0]octadienones.

Authors:  Céline Joie; Kristina Deckers; Gerhard Raabe; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2014-06-01       Impact factor: 3.157

2.  An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel-Crafts/Michael/Michael/Aldol Condensation Sequence.

Authors:  Arne R Philipps; Lars Fritze; Nico Erdmann; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2015-04-02       Impact factor: 3.157

3.  Asymmetric synthesis of highly functionalized tetrahydropyrans via a one-pot organocatalytic Michael/Henry/ketalization sequence.

Authors:  Robert Hahn; Gerhard Raabe; Dieter Enders
Journal:  Org Lett       Date:  2014-06-27       Impact factor: 6.005

4.  A quadruple cascade protocol for the one-pot synthesis of fully-substituted hexahydroisoindolinones from simple substrates.

Authors:  Hong-Bo Zhang; Yong-Chun Luo; Xiu-Qin Hu; Yong-Min Liang; Peng-Fei Xu
Journal:  Beilstein J Org Chem       Date:  2016-02-11       Impact factor: 2.883
  4 in total

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