AlCl3-Promoted Formal [2 + 3]-Cycloaddition of 1,1-Cyclopropane Diesters with N-Benzylic Sulfonamides To Construct Highly Stereoselective Indane Derivatives

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• 作者：Mengyun Zhu ; Jinqian Liu ; Jianjun Yu ; Liangshun Chen ; Chunmei Zhang ; Limin Wang
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：April 4, 2014
• 年：2014
• 卷：16
• 期：7
• 页码：1856-1859
• 全文大小：344K
• 年卷期：v.16,no.7(April 4, 2014)
• ISSN：1523-7052

文摘

An unprecedented AlCl₃-promoted formal [2 + 3]-cycloaddition of 1,1-cyclopropanes with readily available N-benzylic sulfonamides has been developed. Experimental evidence supports an unusual mechanism wherein the donor鈥揳cceptor cyclopropane serves as a source of 2-styrylmalonate rather than the 鈥渃lassical鈥?1,3-dipole. A broad range of 1,1-cyclopropanediesters undergo a carbocation-initiated cyclization reaction with N-benzylic sulfonamides to afford highly functionalized Indane derivatives in a fast and high-yielding procedure.