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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

✍ Scribed by Hiroyuki Izawa; Ryuichi Shirai; Hisashi Kawasaki; Hee-doo Kim; Kenji Koga

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
226 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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