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Iron-Catalyzed Asymmetric Haloazidation of α,β-Unsaturated Ketones: Construction of Organic Azides with Two Vicinal Stereocenters

Pengfei Zhou, Lili Lin, Long Chen, Xia Zhong, Xiaohua Liu and Xiaoming Feng*

*Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China, Email: xmfengscu.edu.cn

P. Zhou, L. Lin, L. Chen, X. Zhong, X. Liu, X. Feng, J. Am. Chem. Soc., 2017, 139, 13414-13419.

DOI: 10.1021/jacs.7b06029


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Abstract

Chiral N,N'-dioxide/Fe(OTf)2 complexes catalyze an unprecedented highly diastereo- and enantioselective bromoazidation of α,β-unsaturated ketones. An array of aryl, heteroaryl, and alkyl substituted α,β-unsaturated ketones were transformed to the corresponding α-bromo-β-azido ketones in high yields with excellent diastereo- and enantioselectivities. The catalytic system was also applicable for chloroazidations and iodoazidations.

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Catalytic Asymmetric Construction of β-Azido Amides and Esters via Haloazidation

P. Zhou, X. Liu, W. Wu, C. Xu, X. Feng, Org. Lett., 2019, 21, 1170-1175.


Key Words

bromination, azidation


ID: J48-Y2017