Literature DB >> 21132061

Intermolecular Cross-Acyloin Reactions by Fluoride-Promoted Additions of O-Silyl Thiazolium Carbinols.

Alex K Mathies1, Anita E Mattson, Karl A Scheidt.   

Abstract

The addition of acyl anion equivalents to aliphatic aldehydes (crossed-acyloin reaction) has been developed. Cesium fluoride with isopropanol as solvent promotes the addition of O-silyl thiazolium carbinols to various aliphatic aldehydes in moderate to good yields. These reactions represent a general procedure for the selective coupling of aliphatic aldehydes by an acyl anion reaction which have been problematic until now.

Entities:  

Year:  2009        PMID： 21132061      PMCID： PMC2995280          DOI： 10.1055/s-0028-1087555

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  20 in total

1.  N-heterocyclic carbenes as organocatalysts.

Authors:  Nicolas Marion; Silvia Díez-González; Steven P Nolan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Thiazolium-catalyzed additions of acylsilanes: a general strategy for acyl anion addition reactions.

Authors:  Anita E Mattson; Ashwin R Bharadwaj; Andrea M Zuhl; Karl A Scheidt
Journal:  J Org Chem       Date:  2006-07-21       Impact factor: 4.354

3.  Kinetics of the thiazolium ion-catalyzed benzoin condensation.

Authors:  M J White; F J Leeper
Journal:  J Org Chem       Date:  2001-07-27       Impact factor: 4.354

4.  Palladium-catalyzed synthesis of aryl ketones by coupling of aryl bromides with an acyl anion equivalent.

Authors:  Akihiro Takemiya; John F Hartwig
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

5.  Stereocontrolled and convergent total synthesis of amphidinolide T3.

Authors:  Li-Sheng Deng; Xiao-Ping Huang; Gang Zhao
Journal:  J Org Chem       Date:  2006-06-09       Impact factor: 4.354

6.  An approach to the synthesis of the phomoidrides.

Authors:  Matthew M Bio; James L Leighton
Journal:  J Org Chem       Date:  2003-03-07       Impact factor: 4.354

7.  Nucleophilic carbenes in asymmetric organocatalysis.

Authors:  Dieter Enders; Tim Balensiefer
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

8.  Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot sila-Stetter/Paal-Knorr strategy.

Authors:  Ashwin R Bharadwaj; Karl A Scheidt
Journal:  Org Lett       Date:  2004-07-08       Impact factor: 6.005

9.  An epoxide intermediate in nucleophilic acylations by thiazolium precursors.

Authors:  Scott Gronert
Journal:  Org Lett       Date:  2007-07-04       Impact factor: 6.005

10.  The thiazolium-catalyzed Sila-Stetter reaction: conjugate addition of acylsilanes to unsaturated esters and ketones.

Authors:  Anita E Mattson; Ashwin R Bharadwaj; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2004-03-03       Impact factor: 15.419
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