Literature DB >> 18758602

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

Dieter Enders1, Jianwei Han, Alexander Henseler.   

Abstract

The asymmetric intermolecular Stetter reaction is catalyzed by a novel triazolium salt derived N-heterocyclic carbene leading to 1,4-diketones in moderate to excellent yields (49-98%) and moderate to good enantioselectivities (56-78% ee), which could be enhanced by one recrystallization to excellent levels (90-99% ee).

Entities:  

Year:  2008        PMID： 18758602     DOI： 10.1039/b809913h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  15 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

2.  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 3.  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

4.  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

5.  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

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

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

7.  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

8.  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

9.  Alpha'-hydroxyenones as mechanistic probes and scope-expanding surrogates for alpha,beta-unsaturated aldehydes in N-heterocyclic carbene-catalyzed reactions.

Authors:  Pei-Chen Chiang; Michael Rommel; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2009-06-24       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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