Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes

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• 作者：Raynold Shenje ; Corey W. Williams ; Katherine M. Francois ; Stefan France
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：December 19, 2014
• 年：2014
• 卷：16
• 期：24
• 页码：6468-6471
• 全文大小：380K
• ISSN：1523-7052

文摘

A chemodivergent, Lewis acid catalyzed allylsilane interrupted formal homo-Nazarov cyclization is disclosed. With catalytic amounts of SnCl₄ and in the presence of allyltrimethylsilane, a formal Hosomi鈥揝akurai-type allylation of the oxyallyl cation intermediate is observed. A variety of functionalized donor鈥揳cceptor cyclopropanes and allylsilanes were shown to be amenable to the reaction transformation and the allyl products were formed in up to 92% yield. Under dilute reaction conditions with stoichiometric SnCl₄ and at reduced temperatures, an unusual formal [3 + 2]-cycloaddition between the allylsilane and the oxyallyl cation occurred to give hexahydrobenzofuran products in up to 69% yield.