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Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Oxime Esters to Cyclopropanecarbonitriles

Bin Shuai, Ping Fang*, Tian-Sheng Mei*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, P. R. of China, Email: mei7900sioc.ac.cn, pfangsioc.ac.cn

B. Shuai, P. Fang, T.-S. Mei, Synlett, 2021, 32, 1637-1641.

DOI: 10.1055/s-0039-1690872 (free Supporting Information)


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Abstract

In a nickel-catalyzed base-promoted rearrangement of cyclobutanone oxime esters to cyclopropanecarbonitriles, the ring opening occurs at the sterically less hindered side. A base-promoted nickelacyclobutane intermediate, formed in situ, is assumed to be involved in the formation of the product.

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Key Words

nickel catalysis, cyclobutanone oxime esters, cyclopropanes, cyclopropanecarbonitriles, ring opening, Favorsky rearrangement


ID: J72-Y2021