SYNTHESIS OF GEOMETRICALLY DEFINED EXOCYCLIC OLEFINS

Authors
BENNANI YL HWANG CK KOCH SSC MARRON KS DARDASHTI LJ BADEA BA NADZAN AM
Citation
Yl. Bennani et al., SYNTHESIS OF GEOMETRICALLY DEFINED EXOCYCLIC OLEFINS, Tetrahedron letters, 37(45), 1996, pp. 8109-8112
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
45
Year of publication
1996
Pages
8109 - 8112
Database
ISI
SICI code
0040-4039(1996)37:45<8109:SOGDEO>2.0.ZU;2-Y
Abstract
The treatment of bicyclic and tricyclic ketones with lithium ethynyl a cetylide, followed by the addition of a catalytic amount of CSA or p-T SA, affords the corresponding exocyclic olefinic ester in good yields, and geometric ratios up to 13:1 favoring the cis olefin. This procedu re represents an addition to the repertoire of olefination methods and can readily be extended to other cyclic and acyclic systems. Copyrigh t (C) 1996 Elsevier Science Ltd