Literature DB >> 21678918

Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: enhancement of catalytic efficiency through bifunctional additives.

Daniel A DiRocco1, Tomislav Rovis.   

Abstract

An asymmetric intermolecular Stetter reaction of enals with nitroalkenes catalyzed by chiral N-heterocyclic carbenes has been developed. The reaction rate and efficiency are profoundly impacted by the presence of catechol. The reaction proceeds with high selectivities and affords good yields of the Stetter product. Internal redox products were not observed despite of the protic conditions. The impact of catechol has been found to be general, facilitating far lower catalyst loadings than were previously achievable.

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Year:  2011        PMID： 21678918      PMCID： PMC3147302          DOI： 10.1021/ja203810b

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  21 in total

1.  The enzymatic asymmetric conjugate umpolung reaction.

Authors:  Carola Dresen; Michael Richter; Martina Pohl; Steffen Lüdeke; Michael Müller
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-03       Impact factor: 15.336

2.  Umpolung catalysts: comparative assessments on reactivities.

Authors:  Bernd Goldfuss; Maria Schumacher
Journal:  J Mol Model       Date:  2005-10-29       Impact factor: 1.810

Review 3.  Organocatalysis by N-heterocyclic carbenes.

Authors:  Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal:  Chem Rev       Date:  2007-10-23       Impact factor: 60.622

4.  N-heterocyclic carbenes as organocatalysts.

Authors:  Nicolas Marion; Silvia Díez-González; Steven P Nolan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Mechanistic investigation of the enantioselective intramolecular stetter reaction: proton transfer is the first irreversible step.

Authors:  Jennifer L Moore; Anthony P Silvestri; Javier Read de Alaniz; Daniel A DiRocco; Tomislav Rovis
Journal:  Org Lett       Date:  2011-02-28       Impact factor: 6.005

6.  Conversion of alpha,beta-unsaturated aldehydes into saturated esters: an Umpolung reaction catalyzed by nucleophilic carbenes.

Authors:  Audrey Chan; Karl A Scheidt
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

7.  The C-F bond as a conformational tool in organic and biological chemistry.

Authors:  Luke Hunter
Journal:  Beilstein J Org Chem       Date:  2010-04-20       Impact factor: 2.883

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.  Asymmetric intermolecular Stetter reactions catalyzed by a novel triazolium derived N-heterocyclic carbene.

Authors:  Dieter Enders; Jianwei Han; Alexander Henseler
Journal:  Chem Commun (Camb)       Date:  2008-07-25       Impact factor: 6.222

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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  21 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

3.  Switchable selectivity in an NHC-catalysed dearomatizing annulation reaction.

Authors:  Chang Guo; Mirco Fleige; Daniel Janssen-Müller; Constantin G Daniliuc; Frank Glorius
Journal:  Nat Chem       Date:  2015-08-31       Impact factor: 24.427

4.  Catalytic Enantioselective Synthesis of 1,4-Keto-Alkenylboronate Esters and 1,4-Dicarbonyls.

Authors:  Michael Z Liang; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-23       Impact factor: 15.336

5.  N-heterocyclic carbene and Brønsted acid cooperative catalysis: asymmetric synthesis of trans-γ-lactams.

Authors:  Xiaodan Zhao; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

6.  Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams.

Authors:  Nicholas A White; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2013-05-28       Impact factor: 15.419

7.  Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Authors:  Ki Po Jang; Gerri E Hutson; Ryne C Johnston; Elizabeth O McCusker; Paul H-Y Cheong; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

Review 8.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

Authors:  Javier Izquierdo; Gerri E Hutson; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

9.  The effect of the N-mesityl group in NHC-catalyzed reactions.

Authors:  Jessada Mahatthananchai; Jeffrey W Bode
Journal:  Chem Sci       Date:  2012-01-01       Impact factor: 9.825

10.  A photoisomerization-coupled asymmetric Stetter reaction: application to the total synthesis of three diastereomers of (-)-cephalimysin A.

Authors:  Stephen P Lathrop; Tomislav Rovis
Journal:  Chem Sci       Date:  2013-04       Impact factor: 9.825
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