Literature DB >> 25929160

Enantioselective β-Protonation by a Cooperative Catalysis Strategy.

Michael H Wang1, Daniel T Cohen1, C Benjamin Schwamb1, Rama K Mishra1, Karl A Scheidt1.   

Abstract

An enantioselective N-heterocyclic carbene (NHC)-catalyzed β-protonation through the orchestration of three distinct organocatalysts has been developed. This cooperative catalyst system enhances both yield and selectivity, compared to only the NHC-catalyzed process. This new method allows for the efficient conversion of a large scope of aryl-oxobutenoates to highly enantioenriched succinate derivatives and demonstrates the benefits of combining different activation modes in organocatalysis.

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Year:  2015        PMID： 25929160      PMCID： PMC4492478          DOI： 10.1021/jacs.5b02887

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


  35 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.  Organocatalytic enantioselective acyl transfer onto racemic as well as meso alcohols, amines, and thiols.

Authors:  Christian E Müller; Peter R Schreiner
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-27       Impact factor: 15.336

4.  The DMAP-catalyzed acetylation of alcohols--a mechanistic study (DMAP = 4-(dimethylamino)pyridine).

Authors:  Shangjie Xu; Ingmar Held; Bernhard Kempf; Herbert Mayr; Wolfgang Steglich; Hendrik Zipse
Journal:  Chemistry       Date:  2005-08-05       Impact factor: 5.236

5.  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

6.  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

Review 7.  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

8.  Impact of solvent polarity on N-heterocyclic carbene-catalyzed beta-protonations of homoenolate equivalents.

Authors:  Brooks E Maki; Eric V Patterson; Christopher J Cramer; Karl A Scheidt
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

9.  Chiral squaramide derivatives are excellent hydrogen bond donor catalysts.

Authors:  Jeremiah P Malerich; Koji Hagihara; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2008-10-11       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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  4 in total

1.  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

2.  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

3.  A Cooperative Hydrogen Bond Donor-Brønsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans.

Authors:  Mark A Maskeri; Matthew J O'Connor; Ashley A Jaworski; Anna V Bay; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-27       Impact factor: 15.336

4.  A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization.

Authors:  Xingkuan Chen; Hongling Wang; Kazuki Doitomi; Chong Yih Ooi; Pengcheng Zheng; Wangsheng Liu; Hao Guo; Song Yang; Bao-An Song; Hajime Hirao; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2017-05-25       Impact factor: 14.919
  4 in total

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