Literature DB >> 22571795

Oxidative γ-addition of enals to trifluoromethyl ketones: enantioselectivity control via Lewis acid/N-heterocyclic carbene cooperative catalysis.

Junming Mo1, Xingkuan Chen, Yonggui Robin Chi.   

Abstract

An oxidative γ-functionalization of enals under N-heterocyclic carbene (NHC) catalysis to give unsaturated δ-lactones is disclosed. Enantioselectivity control involving the relatively remote enal γ-carbon was achieved via Lewis acid [Sc(OTf)(3) or combined Sc(OTf)(3)/Mg(OTf)(2)] and NHC cooperative catalysis.

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Year:  2012        PMID： 22571795     DOI： 10.1021/ja303618z

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


  22 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

3.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

4.  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

5.  Enantioselective β-Protonation by a Cooperative Catalysis Strategy.

Authors:  Michael H Wang; Daniel T Cohen; C Benjamin Schwamb; Rama K Mishra; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

6.  A Cooperative Ternary Catalysis System for Asymmetric Lactonizations of α-Ketoesters.

Authors:  Kathleen J R Murauski; Daniel M Walden; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal:  Adv Synth Catal       Date:  2017-08-14       Impact factor: 5.837

7.  A dual Lewis base activation strategy for enantioselective carbene-catalyzed annulations.

Authors:  Javier Izquierdo; Ane Orue; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-07-11       Impact factor: 15.419

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.  N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes.

Authors:  Xiaodan Zhao; Kyle E Ruhl; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-04       Impact factor: 15.336

10.  A cooperative N-heterocyclic carbene/chiral phosphate catalysis system for allenolate annulations.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-04       Impact factor: 15.336
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