Literature DB >> 25278633

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

Céline Joie1, Kristina Deckers1, Gerhard Raabe1, Dieter Enders1.   

Abstract

A new asymmetric organocatalytic three-component quadruple cascade of α-ketoamides with α,β-unsaturated aldehydes is described. The reaction is catalyzed by the (S)-diphenylprolinol TMS ether catalyst and proceeds via an aza-Michael/aldol condensation/vinylogous Michael/aldol condensation sequence to yield tetraaryl-substituted 2-azabicyclo[3.3.0]octadienone derivatives. The cascade products are obtained with good to very good yields (34-71%), virtually complete diastereoselectivities (>20:1), and very good enantioselectivities (84-97%).

Entities:  

Keywords:  aza-Michael addition; domino reactions; organocatalysis; quadruple cascade; vinylogous Michael addition

Year:  2014        PMID： 25278633      PMCID： PMC4178286          DOI： 10.1055/s-0033-1340982

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


  49 in total

1.  Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins.

Authors:  Madhu Sudan Manna; Vikas Kumar; Santanu Mukherjee
Journal:  Chem Commun (Camb)       Date:  2012-04-18       Impact factor: 6.222

2.  Enantio- and diastereoselective synthesis of piperidines by coupling of four components in a "one-pot" sequence involving diphenylprolinol silyl ether mediated Michael reaction.

Authors:  Tatsuya Urushima; Daisuke Sakamoto; Hayato Ishikawa; Yujiro Hayashi
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

3.  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

4.  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

5.  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

6.  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

7.  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

8.  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 9.  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

10.  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
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  2 in total

1.  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

2.  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
  2 in total

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