Synthesis of Chiral Tetrahydrofurans via Catalytic Asymmetric [3 + 2] Cycloaddition of Heterosubstituted Alkenes with Oxiranes

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• 作者：Xiao Yuan ; Lili Lin ; Weiliang Chen ; Wangbin Wu ; Xiaohua Liu ; Xiaoming Feng
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：81
• 期：3
• 页码：1237-1243
• 全文大小：420K
• ISSN：1520-6904

文摘

An efficient diastereo- and enantioselective [3 + 2] cycloaddition of heterosubstituted alkenes with oxiranes via selective C–C bond cleavage of epoxides has been developed. The reaction was catalyzed by a chiral N,N′-dioxide/Ni(II) catalyst, and a variety of chiral highly substituted tetrahydrofurans were obtained in up to 99% yield, 92/8 dr, and 99% ee.