Literature DB >> 20585467

The Catalytic Asymmetric Intramolecular Stetter Reaction.

Javier Read de Alaniz1, Tomislav Rovis.   

Abstract

This account chronicles our efforts at the development of a catalytic asymmetric Stetter reaction using chiral triazolium salts as small molecule organic catalysts. Advances in the mechanistically related azolium-catalyzed asymmetric benzoin reaction are discussed, particularly as they apply to catalyst design. A chronological treatise of reaction discovery, catalyst optimization and reactivity extension follows.

Entities:  

Year:  2009        PMID: 20585467      PMCID: PMC2888141          DOI: 10.1055/s-0029-1216654

Source DB:  PubMed          Journal:  Synlett        ISSN: 0936-5214            Impact factor:   2.454


  43 in total

1.  Stable Carbenes.

Authors:  Didier Bourissou; Olivier Guerret; François P. Gabbaï; Guy Bertrand
Journal:  Chem Rev       Date:  2000-01-12       Impact factor: 60.622

2.  Enantioselective synthesis of P-stereogenic alkynylphosphine oxides by Rh-catalyzed [2+2+2] cycloaddition.

Authors:  Goushi Nishida; Keiichi Noguchi; Masao Hirano; Ken Tanaka
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

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.  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

5.  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

6.  Enantioselective synthesis of alpha,beta-disubstituted-beta-amino acids.

Authors:  Mukund P Sibi; Narayanasamy Prabagaran; Sandeep G Ghorpade; Craig P Jasperse
Journal:  J Am Chem Soc       Date:  2003-10-01       Impact factor: 15.419

7.  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

8.  N-heterocyclic carbenes: a new concept in organometallic catalysis.

Authors:  Wolfgang A Herrmann
Journal:  Angew Chem Int Ed Engl       Date:  2002-04-15       Impact factor: 15.336

9.  Metallophosphites as umpolung catalysts: the enantioselective cross silyl benzoin reaction.

Authors:  Xin Linghu; Justin R Potnick; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2004-03-17       Impact factor: 15.419

10.  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

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  21 in total

1.  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

2.  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

3.  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 4.  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

5.  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

6.  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

7.  Asymmetric N-Heterocyclic Carbene (NHC) Catalyzed Acyl Anion Reactivity.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  Aldrichimica Acta       Date:  2011       Impact factor: 3.667

8.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors:  Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal:  Adv Synth Catal       Date:  2012-04-19       Impact factor: 5.837

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

10.  Silyl ketene imines: highly versatile nucleophiles for catalytic, asymmetric synthesis.

Authors:  Scott E Denmark; Tyler W Wilson
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-11       Impact factor: 15.336

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