Preparation of carbocycles via base-catalyzed endo-mode cyclization of allenes.
Preparation of carbocycles via base-catalyzed endo-mode cyclization of allenes.
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DOI：
10.1021/jo050729w
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发表时间：
2005-07
期刊：
影响因子：
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通讯作者：
C. Mukai;Norikazu Kuroda;Rie Ukon;Rumiko Itoh
中科院分区：
文献类型：
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作者：
C. Mukai;Norikazu Kuroda;Rie Ukon;Rumiko Itoh
通过1-苯磺酰基联烯与在C1-位上具有活性次甲基的取代基的内模式闭环反应，开发了一种新的和可靠的方法来构建五至七元碳环。三取代的1-苯磺酰基联烯发生类似的内模闭环反应，生成相应的五至七元碳环，而相应的四取代联烯则不能生成六元和七元碳环。此外，引入一个芳环的烷基侧链的起始联烯的结构不仅可以正常大小的碳环，但也是一个八元框架。
A new and reliable procedure for constructing five- to seven-membered carbocycles via an endo-mode ring-closing reaction of 1-phenylsulfonylallenes with a substituent that has a terminal active methine moiety at the C1-position has been developed. Trisubstituted 1-phenylsulfonylallenes underwent a similar endo-mode ring-closing reaction to produce the corresponding five- to seven-membered carbocycles, while the formation of six- and seven-membered carbocycles from the corresponding tetrasubstituted allene was not realized. In addition, the introduction of an aromatic ring to the alkyl side chain of the starting allenes made possible the construction not only of normal-sized carbocycles but also an eight-membered framework.