Selenium-directed stereoselective [2+ 2] cycloaddition reactions promoted by Lewis acids: a novel zwitterionic intermediate

S Yamazaki, H Fujitsuka, S Yamabe…

文献索引：Yamazaki, Shoko; Fujitsuka, Hiroyuki; Yamabe, Shinichi; Tamura, Hatsue Journal of Organic Chemistry, 1992 , vol. 57, # 21 p. 5610 - 5619

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被引用次数: 18

摘要

The reaction of (trimethylsily1) vinyl selenide 1 and (trimethylsi1yl) allenyl selenide 2 with vinyl ketones 3a-c in the presence of a Lewis acid gave cyclobutane derivatives stereoseledively. The reaction of 1 and 3a-c with SnCb was quenched either with EhN to give cyclobutanes 4a-c or with H 2 0 to give acylsilanes 1 la-c. The formation of both products is explained in terms of a zwitterionic intermediate. The cis relationship between ...