Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Substrate-Controlled Chemoselective Reactions of Isocyanoacetates with Amides and Lactams

Substrate-Controlled Chemoselective Reactions of Isocyanoacetates with Amides and Lactams
Jian-Feng Zheng, Tai-Long Shen, Zhen Xu, Xiu-Ning Hu, Dong-Cheng Cai, Pei-Qiang Huang
Versatile and chemoselective C–C bond forming methods for the one-pot transformation of amides into other classes of compounds are highly demanding. In this report, we demonstrate the reductive addition of isocyanoacetates to common amides and lactams to produce 5-methoxyoxazoles or bicyclic imidazolines. This one-pot procedure involves partial reduction of amides with Schwartz reagent and chemoselective addition of the carbon of isocyanide group or α-carbon in isocyanoacetates. The quite different reactivity of the isocyanoacetate is due to the different steric hindrance of the amides and lactams.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01768

DOI: 10.1021/acs.joc.7b01768

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