Literature DB >> 20694237

N-heterocyclic carbene catalysed asymmetric cross-benzoin reactions of heteroaromatic aldehydes with trifluoromethyl ketones.

Dieter Enders1, André Grossmann, Jeanne Fronert, Gerhard Raabe.   

Abstract

A new triazolium salt derived N-heterocyclic carbene catalyses an asymmetric cross-benzoin-type reaction of heteroaromatic aldehydes and various trifluoromethyl ketones in good to excellent yields (69-96%) and moderate to good enantioselectivities (ee = 39-85%). Up to 99% ee can be achieved by recrystallisation.

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Year:  2010        PMID： 20694237     DOI： 10.1039/c0cc02013c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  8 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.  Catalytic asymmetric cross-aza-benzoin reactions of aliphatic aldehydes with N-Boc-protected imines.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-04       Impact factor: 15.336

3.  SNAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.

Authors:  Xiaodan Zhao; Garrett S Glover; Kevin M Oberg; Derek M Dalton; Tomislav Rovis
Journal:  Synlett       Date:  2013-06-17       Impact factor: 2.454

4.  Lithium phosphonate umpolung catalysts: Do fluoro substituents increase the catalytic activity?

Authors:  Anca Gliga; Bernd Goldfuss; Jörg M Neudörfl
Journal:  Beilstein J Org Chem       Date:  2011-08-31       Impact factor: 2.883

5.  Rate and equilibrium constants for the addition of N-heterocyclic carbenes into benzaldehydes: a remarkable 2-substituent effect.

Authors:  Christopher J Collett; Richard S Massey; James E Taylor; Oliver R Maguire; AnnMarie C O'Donoghue; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-23       Impact factor: 15.336

6.  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

7.  Rate and Equilibrium Constants for the Addition of N-Heterocyclic Carbenes into Benzaldehydes: A Remarkable 2-Substituent Effect.

Authors:  Christopher J Collett; Richard S Massey; James E Taylor; Oliver R Maguire; AnnMarie C O'Donoghue; Andrew D Smith
Journal:  Angew Chem Weinheim Bergstr Ger       Date:  2015-04-23

8.  Mechanism and stereoselectivity in NHC-catalyzed β-functionalization of saturated carboxylic ester.

Authors:  Yan Li; Zhiqiang Zhang
Journal:  RSC Adv       Date:  2019-03-06       Impact factor: 4.036
  8 in total

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