Literature DB >> 21280664

Switching regioselectivity in crossed acyloin condensations between aromatic aldehydes and acetaldehyde by altering N-heterocyclic carbene catalysts.

Ming Yu Jin1, Sun Min Kim, Hogyu Han, Do Hyun Ryu, Jung Woon Yang.   

Abstract

An unprecedented high level of regioselectivities (up to 96%) in the intermolecular crossed acyloin condensations of various aromatic aldehydes with acetaldehyde was realized by an appropriate choice of N-heterocyclic carbene catalysts.

Entities:  

Year:  2011        PMID： 21280664     DOI： 10.1021/ol102937w

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  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.  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.  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

5.  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

6.  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

Review 7.  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

8.  Oxidation of Vicinal Diols to α-Hydroxy Ketones with H2O2 and a Simple Manganese Catalyst.

Authors:  Francesco Mecozzi; Jia Jia Dong; Pattama Saisaha; Wesley R Browne
Journal:  European J Org Chem       Date:  2017-12-11
  8 in total

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