Literature DB >> 22489096

An N-heterocyclic carbene/Lewis acid strategy for the stereoselective synthesis of spirooxindole lactones.

Julien Dugal-Tessier1, Elizabeth A O'Bryan, Thomas B H Schroeder, Daniel T Cohen, Karl A Scheidt.   

Abstract

A cooperative catalysis approach for the enantioselective formal [3+2] addition of α,β-unsaturated aldehydes to isatins has been developed. Homoenolate annulations of β-aryl enals catalyzed by an N-heterocyclic carbene (NHC) require the addition of lithium chloride for high levels of enantioselectivity. This NHC-catalyzed annulation has been used for the total synthesis of maremycin B.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22489096      PMCID： PMC3406933          DOI： 10.1002/anie.201201643

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  46 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

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.  Split personality of lithium chloride: recent salt effects in organometallic recipes.

Authors:  Eva Hevia; Robert E Mulvey
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-22       Impact factor: 15.336

4.  Catalytic asymmetric synthesis of substituted 3-hydroxy-2-oxindoles.

Authors:  Nadine V Hanhan; Aziza H Sahin; Toby W Chang; James C Fettinger; Annaliese K Franz
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

5.  Enantioselective N-heterocyclic carbene-catalyzed Michael addition to α,β-unsaturated aldehydes by redox oxidation.

Authors:  Zi-Qiang Rong; Min-Qiang Jia; Shu-Li You
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

6.  A novel classification of Lewis acids on the basis of activity and selectivity.

Authors:  S Kobayashi; T Busujima; S Nagayama
Journal:  Chemistry       Date:  2000-10-02       Impact factor: 5.236

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.  Catalytic Synthesis of gamma-Lactams via direct annulations of enals and N-sulfonylimines.

Authors:  Ming He; Jeffrey W Bode
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

Review 9.  Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

Authors:  Chris V Galliford; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

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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  28 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.  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

5.  Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

Authors:  Daniel T Cohen; Chad C Eichman; Eric M Phillips; Emily R Zarefsky; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-14       Impact factor: 15.336

6.  Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors:  Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

7.  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

8.  A tandem isomerization/prins strategy: iridium(III)/Brønsted acid cooperative catalysis.

Authors:  Vince M Lombardo; Christopher D Thomas; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-11       Impact factor: 15.336

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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