Prev. Article Next Article Table of Contents

Article

The First Sequential Reaction Promoted by Manganese: Complete Stereoselective Synthesis of (E)-α,β-Unsaturated Esters from 2,2-Dichloroesters and Aldehydes

Supporting Info

José M. Concellón,* Humberto Rodríguez-Solla, Pamela Díaz, and Ricardo Llavona

Departamento de Qumica Orgnica e Inorgnica, Facultad de Qumica, Universidad de Oviedo, Julin Clavera 8, 33071 Oviedo, Spain

J. Org. Chem., 2007, 72 (12), pp 4396–4400

DOI: 10.1021/jo070209w

Publication Date (Web): May 15, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jmcg@uniovi.es

Abstract

α,β-Unsaturated esters were obtained with complete control of stereoselectivity utilizing a sequential reaction of dichloroesters with a variety of aldehydes, promoted by active manganese. This methodology is generally applicable, and the C−C double bond can be di- or trisubstituted. A mechanism based on a successive aldol-type reaction/β-elimination is proposed to explain these results.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue June 08, 2007
Received February 1, 2007

Recommend & Share

Related Content

Wittig Reactions in Water Media Employing Stabilized Ylides with Aldehydes. Synthesis of α,β-Unsaturated Esters from Mixing Aldehydes, α-Bromoesters, and Ph₃P in Aqueous NaHCO₃The Journal of Organic Chemistry
- Wittig Reactions in Water Media Employing Stabilized Ylides with Aldehydes. Synthesis of α,β-Unsaturated Esters from Mixing Aldehydes, α-Bromoesters, and Ph₃P in Aqueous NaHCO₃
  Amer El-Batta, Changchun Jiang, Wen Zhao, Robert Anness, Andrew L. Cooksy, and Mikael Bergdahl
  The Journal of Organic Chemistry 2007 72 (14), pp 5244–5259
  Abstract: Water is demonstrated to be an effective medium for the Wittig reaction over a wide range of stabilized ylides and aldehydes. Despite sometimes poor solubility of the reactants, good chemical yields normally ranging from 80 to 98% and high E-selectivities ...
  Abstract | Full Text HTML | Hi-Res PDF
Fe(0)-Mediated Synthesis of Tri- and Tetra-Substituted Olefins from Carbonyls: An Environmentally Friendly Alternative to Cr(II)The Journal of Organic Chemistry
- Fe(0)-Mediated Synthesis of Tri- and Tetra-Substituted Olefins from Carbonyls: An Environmentally Friendly Alternative to Cr(II)
  J. R. Falck, Romain Bejot, Deb K. Barma, Anish Bandyopadhyay, Suju Joseph, and Charles Mioskowski
  The Journal of Organic Chemistry 2006 71 (21), pp 8178–8182
  Abstract: Fe(0) was investigated as a cost-effective, environmentally friendly alternative to Cr(II) for the olefination of carbonyls by activated polyhalides. In many instances, Fe(0) was equivalent or superior to Cr(II). Notably, Fe(0), but not Cr(II), proved ...
  Abstract | Full Text HTML | Hi-Res PDF
Novel Ambiphilic Dichlorocarbenoid Equivalent in Alkene Cyclopropanation and Carbonyl OlefinationThe Journal of Organic Chemistry
- Novel Ambiphilic Dichlorocarbenoid Equivalent in Alkene Cyclopropanation and Carbonyl Olefination
  Ching-Ting Chien, Chia-Chung Tsai, Chi-Hui Tsai, Tsai-Yuan Chang, Ping-Kuei Tsai, Ying-Chuan Wang, and Tu-Hsin Yan
  The Journal of Organic Chemistry 2006 71 (11), pp 4324–4327
  Abstract: The Ti−Mg−dichloromethylene complexes derived from the oxidative addition of CCl₄ to the Mg−TiCl₄ bimetallic species serve as a novel class of ambiphilic dichlorocarbenoid equivalents. Not only is Ti−Mg−dichlorocarbenoid highly selective but also it seems ...
  Abstract | Full Text HTML | Hi-Res PDF

Article

The First Sequential Reaction Promoted by Manganese: Complete Stereoselective Synthesis of (E)-α,β-Unsaturated Esters from 2,2-Dichloroesters and Aldehydes