Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Iron-Catalyzed Carboamination of Olefins: Synthesis of Amines and Disubstituted β-Amino Acids

Iron-Catalyzed Carboamination of Olefins: Synthesis of Amines and Disubstituted β-Amino Acids
Xinhao Zhang, Ting Wang, Hongli Bao, Shaowei Chen, Bo Qian
Intermolecular carboamination of olefins with general alkyl groups is an unsolved problem. Diastereoselective carboamination of acyclic olefins represents an additional challenge in intermolecular carboaminations. We have developed a general alkylamination of vinylarenes and the unprecedented diastereoselective anti-carboamination of unsaturated esters, generating amines and unnatural β-amino acids. This alkylamination is enabled by difunctional alkylating reagents and the iron catalyst. Alkyl diacyl peroxides, readily synthesized from aliphatic acids, serve as both alkylating reagents and internal oxidizing agents. A computational study suggests that addition of a nitrile to the carbocation is the diastereoselectivity-determining step, and hyperconjugation is proposed to account for the highly diastereoselective anti-carboamination.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06590

DOI: 10.1021/jacs.7b06590

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