Stereospecific conversion of iodohydrin derivatives into alkenes by means of an allylsilane-titanium tetrachloride system and its application to stereoretentive deoxygenation of epoxides

Whereas erythro-iodohydrin derivatives provided ( E)-alkenes with high stereoselectivity upon treatment with titanium tetrachloride in the presence of allyltrimethylsilane, the corresponding threo isomers afforded ( Z)-alkenes exclusively. The reaction was applied to the stereoretentive conversion o...

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Bibliographic Details
Published in:Tetrahedron letters 1997-07, Vol.38 (29), p.5161-5164
Main Authors: Yachi, Kentaro, Maeda, Katsuya, Shinokubo, Hiroshi, Oshima, Koichiro
Format: Article
Language:English
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Summary:Whereas erythro-iodohydrin derivatives provided ( E)-alkenes with high stereoselectivity upon treatment with titanium tetrachloride in the presence of allyltrimethylsilane, the corresponding threo isomers afforded ( Z)-alkenes exclusively. The reaction was applied to the stereoretentive conversion of epoxides to alkenes. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01117-9