Regio- and Stereoselectivity in Stannyl- and Silylcupration of Alkynes and Enynes Using Proton Sources

Jean-François Betzer; Ange Pancrazi

doi:10.1055/s-1998-1864

Synlett 1998; 1998(10): 1129-1131
DOI: 10.1055/s-1998-1864

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Regio- and Stereoselectivity in Stannyl- and Silylcupration of Alkynes and Enynes Using Proton Sources

Jean-François Betzer^* , Ange Pancrazi

^*Laboratoire de Synthèse Organique, Ecole Polytechnique, DCSO, 91128 Palaiseau, France; Fax (33)01 69 33 30 10; E-mail: pancrazi@poly.polytechnique.fr

Abstract

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Stannylcupration of alkyne 6 was performed using different proton sources such as phenols, alcohols and water; results showed that the cuprate reagent was not affected during the reaction. In all cases tested in presence of a proton source, the vinylstannane 10 corresponding to a trans addition was not produced, while the distal and proximal isomers 8 and 9 resulting from a cis addition were obtained in good yield. The 8/9 ratio was dependent on the reaction temperature, the acidity and the number of equivalents of the proton source. This study was also extended to the stannylcupration of enynes and silylcupration of alkynes and enynes.

stannylcupration - enyne - alkyne - proton source - methanol - water

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