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[formula: see text] beta-Siloxy unsaturated nitriles are excellent precursors to enolate and nitrile anions that cyclize to cis- and trans-decalins, respectively. The stereoelectronic requirements of endocyclic enolates and exocyclic nitrile anions are complementary, providing cis- and trans-decalins from a common intermediate. This cyclization allows the synthesis of diastereomeric cis- and trans-decalins containing a contiguous array of quaternary-tertiary-quaternary stereocenters.
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Fleming et al. (1999) studied this question.
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