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Wang Y, Zheng C, You SL. Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy. Angew Chem Int Ed Engl. 2017;56(47):15093-15097doi: 10.1002/anie.201708419.
Wang, Y., Zheng, C., & You, S. L. (2017). Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy. Angewandte Chemie (International ed. in English), 56(47), 15093-15097. https://doi.org/10.1002/anie.201708419
Wang, Ye, et al. "Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy." Angewandte Chemie (International ed. in English) vol. 56,47 (2017): 15093-15097. doi: https://doi.org/10.1002/anie.201708419
Wang Y, Zheng C, You SL. Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy. Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15093-15097. doi: 10.1002/anie.201708419. Epub 2017 Oct 24. PMID: 28980373.
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Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15093-15097. doi: 10.1002/anie.201708419. Epub 2017 Oct 24.

Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy.

Angewandte Chemie (International ed. in English)

Ye Wang, Chao Zheng, Shu-Li You

Affiliations

  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
  2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China.

PMID: 28980373 DOI: 10.1002/anie.201708419

Abstract

A desymmetrization strategy was developed involving iridium-catalyzed allylic dearomatization of indoles. The six-membered-ring spiroindolenines contain three contiguous stereogenic centers, including an all-carbon quaternary center, and were obtained in up to 99 % yield with 99 % ee and >95:5 d.r. When treated with a catalytic amount of tosylic acid, six-membered spiroindolenine undergoes an unprecedented six-to-seven-membered ring expansion, affording the corresponding hexahydroazepino[4,5-b]indole.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: asymmetric catalysis; dearomatization; enantioselective synthesis; indoles; iridium catalysts

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