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The conversion of bicyclo[3.3.0]octane-3,7-dione to bicyclo[3.3.0]oct-1-ene-3,7-dione. Symmetry as a complicating factor in synthetic analysis.

โœ Scribed by Steven H Bertz

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
255 KB
Volume
24
Category
Article
ISSN
0040-4039

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Enantioselective deprotonation of the mo
Enantioselective deprotonation of the monoacetals of bicyclo[3.3.0]octan-3,7-dione. An approach to the asymmetric synthesis of chiral synthons for carbacyclins
โœ Hiroyuki Izawa; Ryuichi Shirai; Hisashi Kawasaki; Hee-doo Kim; Kenji Koga ๐Ÿ“‚ Article ๐Ÿ“… 1989 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 226 KB

Kinetic deprotonation of the monoacetals (4) of bicycloE3.3.0loctan-3,7-dione by chiral lithium amides (5) in the presence of excess trimethylsilyl chloride afforded the corresponding silyl enol ethers (6), useful synthons for the synthesis of optically active carbacyclins, in up to 94% ee.