Tetrahedron

Intramolecular diels-alder reactions of silyl acetal-tethered trienes

PJ Ainsworth, D Craig, JC Reader, AMZ Slawin…

Index: Ainsworth, Peter J.; Craig, Donald; Reader, John C.; Slawin, Alexandra M. Z.; White, Andrew J. P.; Williams, Dawid J. Tetrahedron, 1995 , vol. 51, # 42 p. 11601 - 11622

Full Text: HTML

Citation Number: 24

Abstract

The synthesis and intramolecular Diels-Alder reactions of a series of silyl acetal-tethered trienes 4–9 are described. The cycloadditions show complete regioselectivity, and in all but one case give exclusively cis-fused bicyclic products. The selectivities are rationalised in terms of stereoelectronic and steric effects.