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A Versatile and Highly Stereoselective Access to Vinyl Triflates Derived from 1,3-Dicarbonyl and Related Compounds

Simon Specklin, Philippe Bertus, Jean-Marc Weibel and Patrick Pale*

*Laboratoire de Synthse et Ractivit Organiques, associ au CNRS, Institut de Chimie, Universit Louis Pasteur, 4 rue Blaise Pascal, 67000 Strasbourg, France, Email:

S. Specklin, P. Bertus, J.-M. Weibel, P. Pale, J. Org. Chem., 2008, 73, 7845-7848.

DOI: 10.1021/jo8015049


1,3-diketones, β-ketoaldehydes, β-ketoesters, β-ketoamides, β-ketophosphonates and β-ketosulfones were efficiently converted to the corresponding Z vinyl triflates with high stereoselectivity. Precoordination with lithium triflate in dichloromethane and enolization with mild bases followed by trapping with triflic anhydride probably accounted for such high selectivity.

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Key Words

Vinyl Triflates

ID: J42-Y2008-2940