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