Literature DB >> 21721090

Organocatalytic hydroacylation of unactivated alkenes.

Daniel A DiRocco1, Tomislav Rovis.   

Abstract

N-Heterocyclic carbenes interact with aldehydes to generate the Breslow intermediate, a rendering of the prototypical electrophile into a nucleophile (umpolung). Recent work has indicated that these intermediates may also add to simple, unpolarized alkenes. The use of a chiral precatalyst leads to the generation of the derived adducts with high yields and very high selectivities.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 21721090      PMCID： PMC3427711          DOI： 10.1002/anie.201102920

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  11 in total

Review 1.  Carbene catalysts.

Authors:  Jennifer L Moore; Tomislav Rovis
Journal:  Top Curr Chem       Date:  2010

2.  Highly asymmetric NHC-catalyzed hydroacylation of unactivated alkenes.

Authors:  Isabel Piel; Marc Steinmetz; Keiichi Hirano; Roland Fröhlich; Stefan Grimme; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-14       Impact factor: 15.336

3.  Highly enantioselective synthesis of α-amino acid derivatives by an NHC-catalyzed intermolecular Stetter reaction.

Authors:  Thierry Jousseaume; Nathalie E Wurz; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-10       Impact factor: 15.336

4.  N-heterocyclic carbene-catalyzed cascade reaction involving the hydroacylation of unactivated alkynes.

Authors:  Akkattu T Biju; Nathalie E Wurz; Frank Glorius
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

5.  Kinetics of the thiazolium ion-catalyzed benzoin condensation.

Authors:  M J White; F J Leeper
Journal:  J Org Chem       Date:  2001-07-27       Impact factor: 4.354

6.  N-heterocyclic carbene catalyzed nucleophilic substitution reaction for construction of benzopyrones and benzofuranones.

Authors:  Jinmei He; Jiyue Zheng; Jian Liu; Xuegong She; Xinfu Pan
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

7.  A highly enantio- and diastereoselective catalytic intramolecular Stetter reaction.

Authors:  Javier Read de Alaniz; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2005-05-04       Impact factor: 15.419

8.  Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

Authors:  Qin Liu; Stéphane Perreault; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2008-10-04       Impact factor: 15.419

9.  N-heterocyclic carbene-catalyzed hydroacylation of unactivated double bonds.

Authors:  Keiichi Hirano; Akkattu T Biju; Isabel Piel; Frank Glorius
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

10.  Catalytic asymmetric intermolecular stetter reaction of heterocyclic aldehydes with nitroalkenes: backbone fluorination improves selectivity.

Authors:  Daniel A DiRocco; Kevin M Oberg; Derek M Dalton; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419
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  2 in total

1.  Catalytic asymmetric intermolecular Stetter reactions of enolizable aldehydes with nitrostyrenes: computational study provides insight into the success of the catalyst.

Authors:  Daniel A DiRocco; Elizabeth L Noey; K N Houk; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-26       Impact factor: 15.336

Review 2.  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
  2 in total

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