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Bicyclic Allyltin Derivatives through Selective "One Pot" Hydrostannation-Diels Alder Reaction
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1  Departamento de Química and INQUISUR (UNS-CONICET), Universidad Nacional del Sur, Avda. Alem 1253, 8000 Bahía Blanca, Argentina

Abstract: In this paper we report a simple synthetic route to obtain functionalized allyltin derivatives from 1-ethynylcyclohexene (1), through a "one pot" procedure. Radical addition of trineophyltin hydride to 1 leads quantitatively to (Z,E)-1-(2-trineophylstannylvinyl)-cyclohexene (3), a conjugated dienylstannane that, through a [4+2] cycloaddition reaction (Diels -Alder) with activated dienophiles, allows to obtain substituted bicyclic unsaturated products with specific stereochemistry and a trialkylstannyl group in allylic position.
Keywords: bicyclic allyltin; hydrostannation; Diels Alder reaction.