Stereoselective synthesis of cis-decalins via Diels-Alder and double Michael addition of substituted Nazarov reagents

…, R Ruel, KT Hogan, P Deslongchamps

Index: Lavallee, Jean-Francois; Spino, Claude; Ruel, Rejean; Hogan, Keith T.; Deslongchamps, Pierre Canadian Journal of Chemistry, 1992 , vol. 70, # 5 p. 1406 - 1426

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Citation Number: 43

Abstract

The base-catalyzed cycloaddition and double Michael cyclization of substituted Nazarov reagents and of 1-phenylsulfinyl analogs, with 2-carbomethoxy-2-cyclohexen-1-one 1 yielding cis-decalins is reported. The reaction is highly stereoselective affording cis, cis-or cis, t rans-decalins. Mechanistic aspects are briefly discussed.

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