Asymmetric [2,3]-Wittig rearrangement induced by a chiral carbainion whose chirality was transferred from an epoxide

被引：22
|
作者：
Sasaki, M
Higashi, M
Masu, H
Yamaguchi, K
Takeda, K
机构：
[1] Hiroshima Univ, Grad Sch Med Sci, Dept Synthet Organ Chem, Minami Ku, Hiroshima 7348551, Japan
[2] Tokushima Bunri Univ, Kagawa 7692193, Japan
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 26期
关键词：
D O I：
10.1021/ol052544h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] The enantioselective [2,3]-Wittig rearrangement of 1-allyloxy-1-(naphthalen-2-yl)-4-siloxy-2,4-pentadienyl anion, derived from optically enriched 4,5-epoxy-1-(naphthalen-2-yl)-5-silyl-2-pentenyl allyl ether via a base-induced ring opening of the epoxide followed by Brook rearrangement, has been studied. The chirality of the epoxide was transferred to the alcohols in up to 97% ee, depending on the solvent used. The best result was obtained in 1,4-dioxane at a temperature above room temperature.
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收藏
页码：5913 / 5915
页数：3
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