Organic Letters
Organic Letters
5 years ago

Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic CC Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives

Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic CC Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives
Quannan Wang, Fei Huang, Jiang Lou, Zhuqing Liu, Zhengkun Yu
Efficient copper-catalyzed formal carbene migratory insertion into the olefinic C═C bonds of internal olefins, that is, α-oxo ketene N,S-acetals, has been achieved by means of N-tosylhydrazones of ketones as the carbene precursors. Iminofuran derivatives were obtained and further transformed to the corresponding 2(3H)-furanones and 4-oxobutanoates (γ-ketoesters), respectively, under mild conditions. In a similar fashion, α-thioxo ketene N,S-acetals reacted with N-tosylhydrazones of ketones to afford iminothiophenes. It is suggested that formal carbene migratory insertion into the olefinic C═C bond is involved in the overall catalytic cycle, demonstrating a new type of carbene insertion reaction for five-membered heterocycle construction.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01668

DOI: 10.1021/acs.orglett.7b01668

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