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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*

*Department of Chemistry and Biochemistry, San Diego State University, San Diego, California 92182-1030, Email: bergdahlsciences.sdsu.edu

A. El-Batta, C. Jiang, W. Zhao, R. Anness, A. L. Cooksy, M. Bergdahl, J. Org. Chem., 2007, 72, 5244-5259.

DOI: 10.1021/jo070665k (free Supporting Information)


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Abstract

Water is an effective medium for the Wittig reaction over a wide range of stabilized ylides and aldehydes including especially substrates with large hydrophobic entities. Despite sometimes poor solubility of the reactants, good yields and high E-selectivities are achieved, and the rate of the reactions in water is unexpectedly accelerated.

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Key Words

Wittig Reaction, α,β-Unsaturated Esters, Enones


ID: J42-Y2007-2210