Literature DB >> 22399824

N-Heterocyclic Carbene-Promoted Rauhut]Currier Reactions between Vinyl Sulfones and α,β-Unsaturated Aldehydes.

Roxanne L Atienza1, Karl A Scheidt.   

Abstract

N-heterocyclic carbenes (NHCs) promote the addition of 1,1-bis(phenylsulfonyl)ethylene to the α-position of α,β-unsaturated aldehydes. The proposed reaction pathway for this Rauhut-Currier-type reaction includes an unusual conjugate addition of an NHC to a bis-vinyl sulfone.

Entities:  

Year:  2011        PMID： 22399824      PMCID： PMC3293187          DOI： 10.1071/ch11264

Source DB:  PubMed          Journal:  Aust J Chem        ISSN： 0004-9425            Impact factor:   1.321


  61 in total

1.  New Strategies for the Development of an Asymmetric Version of the Baylis-Hillman Reaction This work was supported by the Fonds der Chemischen Industrie (Liebig-scholarship and funds for P. L.). P. L. thanks Prof. Dr. A. de Meijere for his support.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-01       Impact factor: 15.336

2.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

3.  An efficient nucleophilic carbene catalyst for the asymmetric benzoin condensation.

Authors:  Dieter Enders; Ulrike Kallfass
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

4.  Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes.

Authors:  Brooks E Maki; Audrey Chan; Eric M Phillips; Karl A Scheidt
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

5.  Organocatalytic Michael cycloisomerization of bis(enones): the intramolecular Rauhut-Currier reaction.

Authors:  Long-Cheng Wang; Ana Liza Luis; Kyriacos Agapiou; Hye-Young Jang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

6.  N-heterocyclic carbene-catalyzed enantioselective Mannich reactions with alpha-aryloxyacetaldehydes.

Authors:  Yasufumi Kawanaka; Eric M Phillips; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419

7.  Catalytic intramolecular crossed aldehyde--ketone benzoin reactions: a novel synthesis of functionalized preanthraquinones.

Authors:  Yoshifumi Hachisu; Jeffrey W Bode; Keisuke Suzuki
Journal:  J Am Chem Soc       Date:  2003-07-16       Impact factor: 15.419

8.  NHC catalyzed oxidations of aldehydes to esters: chemoselective acylation of alcohols in presence of amines.

Authors:  Suman De Sarkar; Stefan Grimme; Armido Studer
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

9.  Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging Michael acceptors.

Authors:  Sarah Sulzer-Mossé; Alexandre Alexakis; Jiri Mareda; Guillaume Bollot; Gerald Bernardinelli; Yaroslav Filinchuk
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

10.  N-heterocyclic carbene catalyzed aza-Morita-Baylis-Hillman reaction of cyclic enones with N-tosylarylimines.

Authors:  Lin He; Teng-Yue Jian; Song Ye
Journal:  J Org Chem       Date:  2007-08-18       Impact factor: 4.354
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  1 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622
  1 in total

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