Bicyclic allyltin derivatives through selective “one pot” hydrostannation-Diels Alder reaction

ROMINA OCAMPO; SANDRA D. MANDOLESI; LILIANA C. KOLL

Congreso; ECSOC - 14; 2010

MDPI (http://www.sciforum.net/conf/ecsoc-14)

In this paper we report a simple synthetic route to obtain functionalized allyltinderivatives from 1-ethynylcyclohexene (1), through a "one pot" procedure. Radicaladdition 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 obtainsubstituted bicyclic unsaturated products with specific stereochemistry and atrialkylstannyl group in allylic position