Tetrahedron

Asymmetric intramolecular Diels-Alder reactions of sulfoximine-activated trienes

D Craig, NJ Geach, CJ Pearson, AMZ Slawin…

Index: Craig, Donald; Geach, Neil J.; Pearson, Christopher J.; Slawin, Alexandra M. Z.; White, Andrew J. P.; Williams, David J. Tetrahedron, 1995 , vol. 51, # 21 p. 6071 - 6098

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Citation Number: 30

Abstract

A series of N-substituted sulfoximidoyl-1, 6, 8-nonatrienes and 1, 7, 9-decatrienes were synthesised and subjected to thermal intramolecular Diels-Alder (IMDA) reactions to give diastereomeric mixtures of substituted bicyclo [4.3. 0] nonanes and-[4.4. 0] decanes. The reactions showed varying selectivities. Endo/exo selectivity was interpreted in terms of a combination of steric factors and the asynchronous nature of the cycloadditions. ...