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Zhou P, Lin L, Chen L, et al. Iron-Catalyzed Asymmetric Haloazidation of α,β-Unsaturated Ketones: Construction of Organic Azides with Two Vicinal Stereocenters. J Am Chem Soc. 2017;139(38):13414-13419doi: 10.1021/jacs.7b06029.
Zhou, P., Lin, L., Chen, L., Zhong, X., Liu, X., & Feng, X. (2017). Iron-Catalyzed Asymmetric Haloazidation of α,β-Unsaturated Ketones: Construction of Organic Azides with Two Vicinal Stereocenters. Journal of the American Chemical Society, 139(38), 13414-13419. https://doi.org/10.1021/jacs.7b06029
Zhou, Pengfei, et al. "Iron-Catalyzed Asymmetric Haloazidation of α,β-Unsaturated Ketones: Construction of Organic Azides with Two Vicinal Stereocenters." Journal of the American Chemical Society vol. 139,38 (2017): 13414-13419. doi: https://doi.org/10.1021/jacs.7b06029
Zhou P, Lin L, Chen L, Zhong X, Liu X, Feng X. Iron-Catalyzed Asymmetric Haloazidation of α,β-Unsaturated Ketones: Construction of Organic Azides with Two Vicinal Stereocenters. J Am Chem Soc. 2017 Sep 27;139(38):13414-13419. doi: 10.1021/jacs.7b06029. Epub 2017 Sep 15. PMID: 28862434.
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J Am Chem Soc. 2017 Sep 27;139(38):13414-13419. doi: 10.1021/jacs.7b06029. Epub 2017 Sep 15.

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

Journal of the American Chemical Society

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

Affiliations

  1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, China.
  2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, China.

PMID: 28862434 DOI: 10.1021/jacs.7b06029

Abstract

Organic azides play important roles in synthetic chemistry, chemical biology, drug discovery, and material science. Azido-functionalization of alkenes is one of the most efficient procedures for rapid introduction of azide group into organic compounds. But only a few examples have been documented in the catalytic asymmetric version of the azidation of alkenes. Herein, we report an unprecedented highly diastereo- and enantioselective bromoazidation of α,β-unsaturated ketones catalyzed by chiral N,N'-dioxide/Fe(OTf)

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