Literature DB >> 23154931

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

Nathalie E Wurz1, Constantin G Daniliuc, Frank Glorius.   

Abstract

Simple Stetter: A novel N-heterocyclic carbene (NHC) was designed by combining an electron-rich 2,6-dimethoxy substituent and an underestimated yet promising chiral motif. With this NHC in hand, a highly enantioselective intermolecular Stetter reaction of simple acrylates was developed, yielding versatile α-chiral γ-ketoesters. This represents the first catalytic asymmetric route towards these valuable compounds (see scheme).
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2012        PMID: 23154931     DOI: 10.1002/chem.201202432

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  9 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

2.  α-Silyl Amides: Effective Bifunctional Lynchpins for Type I Anion Relay Chemistry.

Authors:  Thomas D Montgomery; Amos B Smith
Journal:  Org Lett       Date:  2017-11-09       Impact factor: 6.005

3.  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

4.  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

5.  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

6.  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

7.  A Sequential Umpolung/Enzymatic Dynamic Kinetic Resolution Strategy for the Synthesis of γ-Lactones.

Authors:  Mark A Maskeri; Malte L Schrader; Karl A Scheidt
Journal:  Chemistry       Date:  2020-04-24       Impact factor: 5.236

Review 8.  Conjugate addition-enantioselective protonation reactions.

Authors:  James P Phelan; Jonathan A Ellman
Journal:  Beilstein J Org Chem       Date:  2016-06-15       Impact factor: 2.883

9.  2-Methyl-1,2,4-triazolo[4,3-a]pyridin-2-ium tetra-fluoroborate.

Authors:  Siping Wei; Li Wang; Qin Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-06-08
  9 in total

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