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Catalytic Generation of Activated Carboxylates from Enals: A Product-Determining Role for the Base

Stephanie S. Sohn and Jeffrey W. Bode*

*Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, Wolfgang Pauli Strasse 10, 8093 Zürich, Switzerland, Email: bodeorg.chem.ethz.ch

S. S. Sohn, J. W. Bode, Org. Lett., 2005, 7, 3873-3876.

DOI: 10.1021/ol051269w



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Abstract

Homoenolates are generated by reaction of N-heterocycle carbenes with enals, leading to carbon-carbon bond formation or activated carboxylates depending on the used base. The design of a new triazolium precatalyst enabled the catalytic, atom-economical redox esterification of enals.

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Catalytic Generation of Activated Carboxylates: Direct, Stereoselective Synthesis of β-Hydroxyesters from Epoxyaldehydes

K. Y.-K. Chow, J. W. Bode, J. Am. Chem. Soc., 2004, 126, 8126-8127.


Key Words

Redox Esterification


ID: J54-Y2005-1290