Tetrahedron

Intramolecular Diels-Alder reactions of internally-substituted trienylsulfones. Synthesis of bicyclo [4.3. 0] and-[4.4. 0] systems possessing a bridgehead sulfonyl group

…, D Craig, AMZ Slawin, AJP White, DJ Williams

Index: Clasby, Martin C.; Craig, Donald; Slawin, Alexandra M. Z.; White, Andrew J. P.; Williams, David J. Tetrahedron, 1995 , vol. 51, # 5 p. 1509 - 1532

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Citation Number: 24

Abstract

A series of trienes possessing internally-activated vinylic sulfone dienophilic groups undergo intramolecular Diels-Alder (IMDA) reaction with high or complete selectivity for the cis-fused products. Incorporation of silyloxy groups within the carbon tether linking the diene and dienophile results in increased IMDA reactivity. The stereochemical outcomes of these processes are rationalised in terms of the preference for an exooriented phenylsulfonyl ...

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