Literature DB >> 24299299

Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Ki Po Jang1, Gerri E Hutson, Ryne C Johnston, Elizabeth O McCusker, Paul H-Y Cheong, Karl A Scheidt.   

Abstract

A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.

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Year:  2013        PMID： 24299299      PMCID： PMC3951019          DOI： 10.1021/ja410932t

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


  63 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.  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

Review 3.  Organocatalysis by N-heterocyclic carbenes.

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

4.  Highly enantioselective intermolecular Stetter reaction of simple acrylates: synthesis of α-chiral γ-ketoesters.

Authors:  Nathalie E Wurz; Constantin G Daniliuc; Frank Glorius
Journal:  Chemistry       Date:  2012-11-14       Impact factor: 5.236

5.  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

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.  Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.

Authors:  Artur Mucha; Paweł Kafarski; Łukasz Berlicki
Journal:  J Med Chem       Date:  2011-08-05       Impact factor: 7.446

8.  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

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

Authors:  Dieter Enders; Jianwei Han; Alexander Henseler
Journal:  Chem Commun (Camb)       Date:  2008-07-25       Impact factor: 6.222

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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  11 in total

Review 1.  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 2.  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

3.  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

4.  Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application.

Authors:  Daniel T Cohen; Ryne C Johnston; Nicholas T Rosson; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-14       Impact factor: 6.222

5.  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

6.  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

7.  Synthesis of dinucleoside acylphosphonites by phosphonodiamidite chemistry and investigation of phosphorus epimerization.

Authors:  William H Hersh
Journal:  Beilstein J Org Chem       Date:  2015-01-30       Impact factor: 2.883

8.  Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation.

Authors:  C Guy Goodman; Morgan M Walker; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2014-12-23       Impact factor: 15.419

9.  Enantioselective functionalization at the C4 position of pyridinium salts through NHC catalysis.

Authors:  Hangyeol Choi; Gangadhar Rao Mathi; Seonghyeok Hong; Sungwoo Hong
Journal:  Nat Commun       Date:  2022-04-01       Impact factor: 17.694

Review 10.  Synthesis of polysubstituted arenes through organocatalytic benzannulation.

Authors:  Qian Zhao; Cheng Peng; Gu Zhan; Bo Han
Journal:  RSC Adv       Date:  2020-11-10       Impact factor: 4.036
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