ENANTIOSELECTIVE DEPROTONATION OF THE MONOACETALS OF BICYCLOOCTAN-3,7-DIONE. AN APPROACH TO THE ASYMMETRIC SYNTHESIS OF CHIRAL SYNTHONS FOR CARBACYCLINS

DOI: 10.1016/S0040-4039(01)93940-1

Source and publish data:

Tetrahedron Letters p. 7221 - 7224 (1989)

Update date:2022-08-04

Topics:

Authors:

Izawa, Hiroyuki

Shirai, Ryuichi

Kawasaki, Hisashi

Kim, Hee-doo

Koga, Kenji

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Article abstract of DOI:10.1016/S0040-4039(01)93940-1

Kinetic deprotonation of the monoacetals (4) of bicyclo<3.3.0>octan-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 94percent ee.

Full text of DOI:10.1016/S0040-4039(01)93940-1

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