Regioselective ring opening of alkylidenecyclopropanone silyl acetals

被引：7

作者：

Fujita, M ^{[1
]}

Fujiwara, K ^{[1
]}

Mouri, H ^{[1
]}

Kazekami, Y ^{[1
]}

Okuyama, T ^{[1
]}

机构：

[1] Univ Hyogo, Himeji Inst Technol, Grad Sch Mat Sci, Kamigori, Hyogo 6781297, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 43期

关键词：

alkylidenecyclopropane; allyl cation; alkylidenecarbene; iodonium salt;

D O I：

10.1016/j.tetlet.2004.09.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylidenecyclopropanone sityl acetals are readily available from the reaction of an alkylidenemethyliodonium salt and ketene silyl acetals in the presence of triethylamine. The three different C-C bonds of the cyclopropane ring can be selectively cleaved with HCl, Lewis acid, or fluoride. The alkylideneallyl cation formed via the cleavage of C2-C3 bond with Lewis acids shows further selectivity in reacting with a nucleophile. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8023 / 8026

页数：4

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