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
收藏
页码：4113 / 4116
页数：4
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