Synthesis of Cyclobutane-Fused Angular Tetracyclic Spiroindolines via Visible-Light-Promoted Intramolecular Dearomatization of Indole Derivatives
An intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cycloaddition was achieved via energy transfer mechanism. The highly strained cyclobutane-fused angular tetracyclic spiroindolines, which were typically unattainable under thermal conditions, could be direc...
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| Published in | Journal of the American Chemical Society Vol. 141; no. 6; pp. 2636 - 2644 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
13.02.2019
Amer Chemical Soc |
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| Abstract | An intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cycloaddition was achieved via energy transfer mechanism. The highly strained cyclobutane-fused angular tetracyclic spiroindolines, which were typically unattainable under thermal conditions, could be directly accessed in high yields (up to 99%) with excellent diastereoselectivity (>20:1 dr) under mild conditions. The method was also compatible with diverse functional groups and amenable to flexible transformations. In addition, DFT calculations provided guidance on the rational design of substrates and deep understanding of the reaction pathways. This process constituted a rare example of indole functionalization by exploiting visible-light-induced reactivity at the excited states. |
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| AbstractList | An intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cycloaddition was achieved via energy transfer mechanism. The highly strained cyclobutane-fused angular tetracyclic spiroindolines, which were typically unattainable under thermal conditions, could be directly accessed in high yields (up to 99%) with excellent diastereoselectivity (>20:1 dr) under mild conditions. The method was also compatible with diverse functional groups and amenable to flexible transformations. In addition, DFT calculations provided guidance on the rational design of substrates and deep understanding of the reaction pathways. This process constituted a rare example of indole functionalization by exploiting visible-light-induced reactivity at the excited states. An intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cycloaddition was achieved via energy transfer mechanism. The highly strained cyclobutane-fused angular tetracyclic spiroindolines, which were typically unattainable under thermal conditions, could be directly accessed in high yields (up to 99%) with excellent diastereoselectivity (>20:1 dr) under mild conditions. The method was also compatible with diverse functional groups and amenable to flexible transformations. In addition, DFT calculations provided guidance on the rational design of substrates and deep understanding of the reaction pathways. This process constituted a rare example of indole functionalization by exploiting visible-light-induced reactivity at the excited states.An intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cycloaddition was achieved via energy transfer mechanism. The highly strained cyclobutane-fused angular tetracyclic spiroindolines, which were typically unattainable under thermal conditions, could be directly accessed in high yields (up to 99%) with excellent diastereoselectivity (>20:1 dr) under mild conditions. The method was also compatible with diverse functional groups and amenable to flexible transformations. In addition, DFT calculations provided guidance on the rational design of substrates and deep understanding of the reaction pathways. This process constituted a rare example of indole functionalization by exploiting visible-light-induced reactivity at the excited states. An intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cyclo-addition was achieved via energy transfer mechanism. The highly strained cyclobutane-fused angular tetracyclic spiroindolines, which were typically unattainable under thermal conditions, could be directly accessed in high yields (up to 99%) with excellent diastereoselectivity (>20:1 dr) under mild conditions. The method was also compatible with diverse functional groups and amenable to flexible transformations. In addition, DFT calculations provided guidance on the rational design of substrates and deep understanding of the reaction pathways. This process constituted a rare example of indole functionalization by exploiting visible-light-induced reactivity at the excited states. |
| Author | Zheng, Chao Zhang, Xiao You, Shu-Li Zhu, Min |
| AuthorAffiliation | State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry School of Physical Science and Technology ShanghaiTech University |
| AuthorAffiliation_xml | – name: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry – name: ShanghaiTech University – name: School of Physical Science and Technology |
| Author_xml | – sequence: 1 givenname: Min surname: Zhu fullname: Zhu, Min organization: ShanghaiTech University – sequence: 2 givenname: Chao orcidid: 0000-0002-7349-262X surname: Zheng fullname: Zheng, Chao email: zhengchao@sioc.ac.cn organization: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry – sequence: 3 givenname: Xiao surname: Zhang fullname: Zhang, Xiao email: zhangxiao@sioc.ac.cn organization: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry – sequence: 4 givenname: Shu-Li orcidid: 0000-0003-4586-8359 surname: You fullname: You, Shu-Li email: slyou@sioc.ac.cn organization: ShanghaiTech University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30653315$$D View this record in MEDLINE/PubMed |
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| Snippet | An intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cycloaddition was achieved via energy transfer mechanism. The... An intramolecular dearomatization of indole derivatives based on visible-light-promoted [2+2] cyclo-addition was achieved via energy transfer mechanism. The... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary cycloaddition reactions diastereoselectivity energy transfer moieties Physical Sciences Science & Technology |
| Title | Synthesis of Cyclobutane-Fused Angular Tetracyclic Spiroindolines via Visible-Light-Promoted Intramolecular Dearomatization of Indole Derivatives |
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