title: beta-Siloxy unsaturated nitriles: stereoselective cyclizations to cis- and trans-decalins.
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.
authors.affiliation: Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282, USA. flemingf@duq.edu
authors.forename: F F
authors.initials: FF
authors.lastname: Fleming
authors.forename: B C
authors.initials: BC
authors.lastname: Shook
authors.forename: T
authors.initials: T
authors.lastname: Jiang
authors.forename: O W
authors.initials: OW
authors.lastname: Steward
mesh_terms: D003500:Cyclization; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009281:Naphthalenes; D009570:Nitriles; C007229:decalin