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Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy.
Angew Chem Int Ed Engl. 2017 11 20; 56(47):15093-15097.AC

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wang Y
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.
Zheng C
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.
You SL
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. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

28980373

Citation

Wang, Ye, et al. "Iridium-Catalyzed Asymmetric Allylic Dearomatization By a Desymmetrization Strategy." Angewandte Chemie (International Ed. in English), vol. 56, no. 47, 2017, pp. 15093-15097.
Wang Y, Zheng C, You SL. Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy. Angew Chem Int Ed Engl. 2017;56(47):15093-15097.
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 Y, Zheng C, You SL. Iridium-Catalyzed Asymmetric Allylic Dearomatization By a Desymmetrization Strategy. Angew Chem Int Ed Engl. 2017 11 20;56(47):15093-15097. PubMed PMID: 28980373.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy. AU - Wang,Ye, AU - Zheng,Chao, AU - You,Shu-Li, Y1 - 2017/10/24/ PY - 2017/08/17/received PY - 2017/10/6/pubmed PY - 2017/10/6/medline PY - 2017/10/6/entrez KW - asymmetric catalysis KW - dearomatization KW - enantioselective synthesis KW - indoles KW - iridium catalysts SP - 15093 EP - 15097 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 56 IS - 47 N2 - 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. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/28980373/Iridium_Catalyzed_Asymmetric_Allylic_Dearomatization_by_a_Desymmetrization_Strategy_ DB - PRIME DP - Unbound Medicine ER -
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