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Synlett 1996; 1996(8): 755-756
DOI: 10.1055/s-1996-5539
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Regio- and Stereocontrolled Hydrostannation of (E) and (Z)-Chloroenynes. An Efficient Preparation of Chlorodienyl Tributyltin Reagents

Mouâd Alami* , Fabiola Ferri
  • *Ecole Normale Supérieure, Département de Chimie, 24 rue Lhomond, 75231 Paris Cedex 05, France, Fax: (+33) 1 47 07 68 56
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Publication Date:
31 December 2000 (online)

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(E) and (Z)-chloroenynes undergo rapid addition of tributyltin hydride in the presence of a catalytic amount of palladium complex to give regio- and stereoselectively chlorodienyl stannanes of general formula A in good to excellent isolated yields. Hydrostannation of conjugated (Z)-1,3-enynes has also been performed and showed to be remarkably regioselective.

Hydrostannation - palladium - chlorodienyl stannanes - dienyl stannanes - chloroenynes