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

OCAMPO, R.A.; MANDOLESI, S.D.; KOLL, L.C.

Arkivoc

ARKAT

Año: 2011 vol. vii p. 195 - 209

1424-6376

In this paper we report a simple "one pot" procedure to functionalized allyltin derivatives from 1- ethynylcyclohexene. Radical addition of trineophyltin hydride gives quantitatively to (Z,E)-1-(2- trineophylstannylvinyl)cyclohexene, a conjugated dienyl-stannane that, via a [4+2] cycloaddition reaction (Diels-Alder) with activated dienophiles, affords substituted bicyclic unsaturated products with specific stereochemistry and a trialkylstannyl group in allylic position. The Stille reaction of the allyltin compound enables the synthesis of aryl substituted bicyclic compounds in moderate to good yields (48-85%).