Regioselective reactions of 1-alkylidene-2-oxyallyl cations with furan: Control of [4+3] cycloaddition, [3+2] cycloaddition, and electrophilic substitution

被引：21

作者：

Fujita, Morifumi ^{[1
]}

Oshima, Makoto ^{[1
]}

Okuno, Sakuro ^{[1
]}

Sugimura, Takashi ^{[1
]}

Okuyama, Tadashi ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 18期

关键词：

D O I：

10.1021/ol061655t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring opening of alkylidenecyclopropanone acetal under acidic conditions produces the 1-alkylidene-2-oxyallyl cation as an intermediate, which reacts with furan to give the [3+2] and [4+3] cycloadducts as well as an electrophilic substitution product. The product distribution is controlled by the oxy substituents of the cation and by the solvent employed.

引用

页码：4113 / 4116

页数：4

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