Regioselective reactions of 1-alkylidene-2-oxyallyl cations with furan: control of [4 + 3] cycloaddition, [3 + 2] cycloaddition, and electrophilic substitution.
Regioselective reactions of 1-alkylidene-2-oxyallyl cations with furan: control of [4 + 3] cycloaddition, [3 + 2] cycloaddition, and electrophilic substitution.
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DOI：
10.1021/ol061655t
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发表时间：
2006-08
期刊：
影响因子：
5.2
通讯作者：
Morifumi Fujita;M. Oshima;Sakuro Okuno;T. Sugimura;T. Okuyama
中科院分区：
文献类型：
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作者：
Morifumi Fujita;M. Oshima;Sakuro Okuno;T. Sugimura;T. Okuyama
烷基烷环丙酮缩醛在酸性条件下开环生成1-烷基烷-2-氧烯丙基阳离子作为中间体，与呋喃反应生成[3 + 2]和[4 + 3]环加合物以及亲电取代产物。产物的分布受阳离子的氧取代基和所用溶剂的控制。
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.