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

Bo Qian, Shaowei Chen, Ting Wang, Xinhao Zhang* and Hongli Bao*

*Peking University Shenzhen Graduate School, Shenzhen 518055; University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, China, Email: zhangxhpkusz.edu.cn, hlbaofjirsm.ac.cn

B. Qian, S. Chen, T. Wang, X. Zhang, H. Bao, J. Am. Chem. Soc., 2017, 139, 13076-13082.

DOI: 10.1021/jacs.7b06590 (free Supporting Information)


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Abstract

A general alkylamination of vinylarenes and an unprecedented diastereoselective anti-carboamination of unsaturated esters provide amines and unnatural β-amino acids. This alkylamination is enabled by an iron catalyst and alkyl diacyl peroxides, that serve as both alkylating reagents and internal oxidizing agents.


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proposed mechanism



Key Words

Ritter Reaction, Alkylation, β-Amino Acids (amination, alkylation)


ID: J48-Y2017