Iridium‐Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy
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....
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| Published in | Angewandte Chemie International Edition Vol. 56; no. 47; pp. 15093 - 15097 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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20.11.2017
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| Edition | International ed. in English |
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| 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.
The Legend of Spiro: An iridium‐catalyzed desymmetrization reaction involving allylic dearomatization of indoles was developed. The six‐membered‐ring spiroindolenines 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 six‐to‐seven‐membered ring expansion, yielding hexahydroazepino[4,5‐b]indole. |
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| AbstractList | 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. 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. 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.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. 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. The Legend of Spiro: An iridium‐catalyzed desymmetrization reaction involving allylic dearomatization of indoles was developed. The six‐membered‐ring spiroindolenines 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 six‐to‐seven‐membered ring expansion, yielding hexahydroazepino[4,5‐b]indole. |
| Author | Zheng, Chao Wang, Ye You, Shu‐Li |
| Author_xml | – sequence: 1 givenname: Ye surname: Wang fullname: Wang, Ye organization: University of Chinese Academy of Sciences, Chinese Academy of Sciences – sequence: 2 givenname: Chao surname: Zheng fullname: Zheng, Chao organization: University of Chinese Academy of Sciences, Chinese Academy of Sciences – sequence: 3 givenname: Shu‐Li orcidid: 0000-0003-4586-8359 surname: You fullname: You, Shu‐Li email: slyou@sioc.ac.cn organization: Collaborative Innovation Center of Chemical Science and Engineering |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28980373$$D View this record in MEDLINE/PubMed |
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| Copyright | 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | enantioselective synthesis indoles asymmetric catalysis iridium catalysts dearomatization |
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| Snippet | A desymmetrization strategy was developed involving iridium‐catalyzed allylic dearomatization of indoles. The six‐membered‐ring spiroindolenines contain three... A desymmetrization strategy was developed involving iridium-catalyzed allylic dearomatization of indoles. The six-membered-ring spiroindolenines contain three... |
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| SubjectTerms | asymmetric catalysis Catalysis dearomatization enantioselective synthesis Indoles Iridium iridium catalysts |
| Title | Iridium‐Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy |
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