Literature DB >> 18834123

Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

Qin Liu1, Stéphane Perreault, Tomislav Rovis.   

Abstract

An asymmetric intermolecular Stetter reaction of glyoxamide and alkylidenemalonates has been developed. Catalyzed by a novel N-heterocyclic carbene, the Stetter adducts are formed in good yield and excellent enantioselectivity. The presence of a sensitive epimerizable stereocenter is tolerated under these mildly basic reaction conditions if a bulky amine base is used. The products may be further elaborated to provide synthetically useful intermediates.

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Year:  2008        PMID： 18834123      PMCID： PMC2684863          DOI： 10.1021/ja805680z

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


  19 in total

1.  An efficient synthesis of achiral and chiral 1,2,4-triazolium salts: bench stable precursors for N-heterocyclic carbenes.

Authors:  Mark S Kerr; Javier Read de Alaniz; Tomislav Rovis
Journal:  J Org Chem       Date:  2005-07-08       Impact factor: 4.354

Review 2.  Organocatalysis by N-heterocyclic carbenes.

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

3.  Towards the total synthesis of FD-838: modular enantioselective assembly of the core.

Authors:  Arturo Orellana; Tomislav Rovis
Journal:  Chem Commun (Camb)       Date:  2008-02-14       Impact factor: 6.222

4.  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

5.  Nucleophilic carbenes in asymmetric organocatalysis.

Authors:  Dieter Enders; Tim Balensiefer
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

6.  Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst.

Authors:  Christopher Uyeda; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2008-06-25       Impact factor: 15.419

7.  Metallophosphite-catalyzed asymmetric acylation of alpha,beta-unsaturated amides.

Authors:  Mary R Nahm; Justin R Potnick; Peter S White; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

8.  Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction.

Authors:  Qin Liu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-03-01       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.  The thiazolium-catalyzed Sila-Stetter reaction: conjugate addition of acylsilanes to unsaturated esters and ketones.

Authors:  Anita E Mattson; Ashwin R Bharadwaj; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2004-03-03       Impact factor: 15.419
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  35 in total

1.  Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation.

Authors:  Kimberly M Steward; Emily C Gentry; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2012-04-17       Impact factor: 15.419

2.  Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.

Authors:  Claire M Filloux; Stephen P Lathrop; Tomislav Rovis
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-16       Impact factor: 11.205

3.  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

4.  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

Review 5.  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

6.  Organocatalytic hydroacylation of unactivated alkenes.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-30       Impact factor: 15.336

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

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-06-16       Impact factor: 15.419

8.  Quantum mechanical investigation of the effect of catalyst fluorination in the intermolecular asymmetric Stetter reaction.

Authors:  Joann M Um; Daniel A DiRocco; Elizabeth L Noey; Tomislav Rovis; K N Houk
Journal:  J Am Chem Soc       Date:  2011-07-06       Impact factor: 15.419

9.  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 10.  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
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