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Synfacts 2007(10): 1059-1059  
DOI: 10.1055/s-2007-963855
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Temperature Effects on Olefin Geometry in the HWE Condensation

Contributor(s): Mark Lautens, Michael Langer
J. S. Yu, D. F. Wiemer*
University of Iowa, Iowa City, USA
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Publikationsdatum:
07. November 2007 (online)

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Significance

The Horner-Wadsworth-Emmons (HWE) condensation is an important reaction to generate Michael systems with a defined stereochemistry on the double bond. In this paper the effect of the olefin geometry in relation to the temperature is reexamined. For example, depending on the conditions after the addition of reactants, either the E- or Z-isomers are formed in high selectivities.