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beta-Siloxy unsaturated nitriles: stereoselective cyclizations to cis- and trans-decalins
F F Fleming1, B C Shook, T Jiang
1Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282, USA. flemingf@duq.edu
Organic Letters
|June 3, 2000
Abstract:
[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.