Literature DB >> 19950884

Highly enantioselective benzoin condensation reactions involving a bifunctional protic pentafluorophenyl-substituted triazolium precatalyst.

Louise Baragwanath1, Christopher A Rose, Kirsten Zeitler, Stephen J Connon.   

Abstract

Improved catalyst design by incorporating a hydrogen bond donating substituent to improve enantiocontrol together with an acidifying pentafluorophenyl substituent to enhance catalyst efficiency results in a triazolium ion precatalyst that promotes the asymmetric archetypal benzoin condensation with excellent efficiency and unprecedented enantioselectivity.

Entities:  

Year:  2009        PMID： 19950884     DOI： 10.1021/jo902018j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 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.  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

3.  N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters.

Authors:  Takuya Uno; Yusuke Kobayashi; Yoshiji Takemoto
Journal:  Beilstein J Org Chem       Date:  2012-09-10       Impact factor: 2.883

4.  Dynamic kinetic asymmetric cross-benzoin additions of β-stereogenic α-keto esters.

Authors:  C Guy Goodman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2014-10-09       Impact factor: 15.419

5.  Application of Chan-Lam cross coupling for the synthesis of N-heterocyclic carbene precursors bearing strong electron donating or withdrawing groups.

Authors:  Liliang Huang; Chengxiang He; Zhihua Sun
Journal:  Sci Rep       Date:  2015-07-23       Impact factor: 4.379

6.  Catalytic Preparation of 1-Aryl-Substituted 1,2,4-Triazolium Salts.

Authors:  Scott M Hutchinson; Luis G Ardón-Muñoz; Margarita L Ratliff; Jeanne L Bolliger
Journal:  ACS Omega       Date:  2019-10-18

7.  The Role of the Fused Ring in Bicyclic Triazolium Organocatalysts: Kinetic, X-ray, and DFT Insights.

Authors:  Jiayun Zhu; Inmaculada Moreno; Peter Quinn; Dmitry S Yufit; Lijuan Song; Claire M Young; Zhuan Duan; Andrew R Tyler; Paul G Waddell; Michael J Hall; Michael R Probert; Andrew D Smith; AnnMarie C O'Donoghue
Journal:  J Org Chem       Date:  2022-03-01       Impact factor: 4.354

Review 8.  Mechanochemical Organocatalysis: Do High Enantioselectivities Contradict What We Might Expect?

Authors:  Matthew T J Williams; Louis C Morrill; Duncan L Browne
Journal:  ChemSusChem       Date:  2021-12-09       Impact factor: 9.140

Review 9.  Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions.

Authors:  Rajeev S Menon; Akkattu T Biju; Vijay Nair
Journal:  Beilstein J Org Chem       Date:  2016-03-09       Impact factor: 2.883

10.  Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine.

Authors:  Guo-Tai Li; Qing Gu; Shu-Li You
Journal:  Chem Sci       Date:  2015-04-30       Impact factor: 9.825
  10 in total

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