Literature DB >> 26413259

Cooperative Lewis acid/N-heterocyclic carbene catalysis.

Daniel T Cohen1, Karl A Scheidt1.   

Abstract

Lewis acid activation with N-heterocyclic carbene (NHC) catalysis has presented new opportunities for enantioselective reaction development. Recent findings illustrate that Lewis acids can play an important role in homoenolate annulations by: enhancement of the reactivity, reversal of the diastereo- or regioselectivity, and activation of previously inactive electrophiles. Additionally, the incorporation of a Lewis acid into Brønsted base-catalyzed conjugate addition allowed for an increase in yields.

Entities:  

Year:  2012        PMID： 26413259      PMCID： PMC4583212          DOI： 10.1039/C1SC00621E

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  37 in total

1.  Discovering New Reactions with N-Heterocyclic Carbene Catalysis.

Authors:  Eric M Phillips; Audrey Chan; Karl A Scheidt
Journal:  Aldrichimica Acta       Date:  2009       Impact factor: 3.667

2.  Imidazolinium salts as catalysts for the ring-opening alkylation of meso epoxides by alkylaluminum complexes.

Authors:  H Zhou; E J Campbell; S T Nguyen
Journal:  Org Lett       Date:  2001-07-12       Impact factor: 6.005

3.  Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions.

Authors:  Pei-Chen Chiang; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2007-03-03       Impact factor: 15.419

Review 4.  Organocatalysis by N-heterocyclic carbenes.

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

5.  Organocatalytic iminium ion/carbene reaction cascade for the formation of optically active 2,4-disubstituted cyclopentenones.

Authors:  Christian Borch Jacobsen; Kim L Jensen; Jonas Udmark; Karl Anker Jørgensen
Journal:  Org Lett       Date:  2011-08-19       Impact factor: 6.005

6.  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

7.  N-heterocyclic carbene-catalyzed conjugate additions of alcohols.

Authors:  Eric M Phillips; Matthias Riedrich; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

8.  Enantioselective synthesis of alpha,alpha-disubstituted cyclopentenes by an N-heterocyclic carbene-catalyzed desymmetrization of 1,3-diketones.

Authors:  Manabu Wadamoto; Eric M Phillips; Troy E Reynolds; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419

9.  Amide enolate additions to acylsilanes: in situ generation of unusual and stereoselective homoenolate equivalents.

Authors:  Robert B Lettan; Chris V Galliford; Chase C Woodward; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419

10.  Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to gamma-lactams.

Authors:  Dustin E A Raup; Benoit Cardinal-David; Dane Holte; Karl A Scheidt
Journal:  Nat Chem       Date:  2010-07-18       Impact factor: 24.427
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  34 in total

1.  A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

Authors:  Kun Liu; M Todd Hovey; Karl A Scheidt
Journal:  Chem Sci       Date:  2014-10-01       Impact factor: 9.825

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

Review 3.  The ever-expanding role of asymmetric covalent organocatalysis in scalable, natural product synthesis.

Authors:  Mikail E Abbasov; Daniel Romo
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

4.  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

5.  Carbene-Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones.

Authors:  Ansoo Lee; Joshua L Zhu; Taisiia Feoktistova; Alexander C Brueckner; Paul H-Y Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

6.  N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.

Authors:  Dian-Feng Chen; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2016-11-18       Impact factor: 3.157

7.  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

8.  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

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.  Oxidatively Initiated NHC-Catalyzed Enantioselective Synthesis of 3,4-Disubstituted Cyclopentanones from Enals.

Authors:  Nicholas A White; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-08-10       Impact factor: 15.419
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