Diastereoselective production of homoallylic alcohols bearing quaternary centers from γ-substituted allylic indiums and ketones

被引：25

作者：

Babu, Srinivasarao Arulananda ^{[1
]}

Yasuda, Makoto ^{[1
]}

Baba, Akio ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 26期

关键词：

D O I：

10.1021/jo701899j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Highly stereoselective In-employed addition of gamma-substituted allylic halides (cyclohexenyl halides, cinnamyl halides, and ethyl 4-bromocrotonate) to ketones is established to produce homoallyl alcohols bearing quaternary centers. The reactivity patterns and relative stability of allylic indiums were studied. The addition of water characteristically affected the reactions. Cyclohexenyl indium addition was completely disturbed, but a clear reaction was observed in the cinnamyl and crotonate- indium addition. In the case of ethyl 4-bromocrotonate, an interesting conversion of a gamma-adduct into an a-adduct was observed in anhydrous conditions.

引用

页码：10264 / 10267

页数：4

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