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Synlett 2000; 2000(8): 1119-1122
DOI: 10.1055/s-2000-6764
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Diels-Alder Reactions of 4,4-Disubstituted 2-Cyano-2,5-cyclohexadienones. A Facile Approach to the Angularly Substituted cis-Decalin System

Hsing-Jang Liu* , Judy Yip
  • *Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, R.O.C.; Fax + 886-3-5 72 07 11; E-mail: hjliu@mx.nthu.edu.tw
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Publication Date:
31 December 2000 (online)

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4,4-Disubstituted 2-cyano-2,5-cyclohexadienones 1 and 2 were found to add efficiently to a variety of conjugated dienes under zinc chloride catalysis. On exposure to lithium naphthalenide, the adducts thus obtained were shown to undergo facile reductive decyanation, and the ensuing enolate ions readily trapped with a variety of alkylating agents to provide angularly substituted, highly functionalized cis-decalin derivatives.

cycloaddition - reduction - alkylation - cyano compounds - ketones