Carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles
A carbene-catalyzed enantioselective cascade reaction of substituted methylenemalononitriles and α-bromoenals is disclosed. Key steps of this cascade process include a formal [4 + 2] cycloaddition, aldol reaction, and intramolecular lactonization. Our reaction offers streamlined and highly stereosel...
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sg-ntu-dr.10356-1486412023-02-28T19:57:53Z Carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles Mou, Chengli Zhou, Liejin Song, Runjiang Chai, Huifang Hao, Lin Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Chemical Reactions Reaction Products A carbene-catalyzed enantioselective cascade reaction of substituted methylenemalononitriles and α-bromoenals is disclosed. Key steps of this cascade process include a formal [4 + 2] cycloaddition, aldol reaction, and intramolecular lactonization. Our reaction offers streamlined and highly stereoselective access to complex tetrahydrocarbazole derivatives, with simultaneous formation of four chemical bonds and four chiral centers. Ministry of Education (MOE) National Research Foundation (NRF) Accepted version We thank Dr. Yongxin Li (NTU) for assistance with X-ray structure analysis. We acknowledge financial support by the Singapore National Research Foundation (NRF-NRFI2016- 06), the Ministry of Education of Singapore (RG 1/18; RG 5/ 19; MOE2018-T3-1-003), an A*STAR Individual Research Grant (A1783c0008; A1783c0010), GSK-EDB Trust Fund, a Nanyang Research Award Grant, and Nanyang Technological University; the Guizhou Province First-Class Disciplines Project (Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008, Guizhou University of Traditional Chinese Medicine (China), QMYY [2017]101 (China); the National Natural Science Foundation of China (Nos. 21772029, 21901233), the National Key Technologies R&D Program (No. 2014BAD23B01), the “Thousand Talent Plan”, the 10 Talent Plan (Shicengci) of Guizhou Province [2016]5649, and Guizhou University, Department of Science and Technology of Guizhou Province [2019]1020, Undergraduate Innovation and Pioneer Training Program, Guizhou University of Traditional Chinese Medicine 2018(31), Program of Introduc- ing Talents of Discipline to Universities of China (111 Program, D20023). 2021-05-18T04:34:34Z 2021-05-18T04:34:34Z 2020 Journal Article Mou, C., Zhou, L., Song, R., Chai, H., Hao, L. & Chi, R. Y. (2020). Carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles. Organic Letters, 22(7), 2542-2547. https://dx.doi.org/10.1021/acs.orglett.0c00418 1523-7052 0000-0003-0573-257X https://hdl.handle.net/10356/148641 10.1021/acs.orglett.0c00418 32191040 2-s2.0-85082310813 7 22 2542 2547 en Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.0c00418 application/pdf |
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Science::Chemistry Chemical Reactions Reaction Products Mou, Chengli Zhou, Liejin Song, Runjiang Chai, Huifang Hao, Lin Chi, Robin Yonggui Carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles |
| description |
A carbene-catalyzed enantioselective cascade reaction of substituted methylenemalononitriles and α-bromoenals is disclosed. Key steps of this cascade process include a formal [4 + 2] cycloaddition, aldol reaction, and intramolecular lactonization. Our reaction offers streamlined and highly stereoselective access to complex tetrahydrocarbazole derivatives, with simultaneous formation of four chemical bonds and four chiral centers. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Mou, Chengli Zhou, Liejin Song, Runjiang Chai, Huifang Hao, Lin Chi, Robin Yonggui |
| format |
Article |
| author |
Mou, Chengli Zhou, Liejin Song, Runjiang Chai, Huifang Hao, Lin Chi, Robin Yonggui |
| author_sort |
Mou, Chengli |
| title |
Carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles |
| title_short |
Carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles |
| title_full |
Carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles |
| title_fullStr |
Carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles |
| title_full_unstemmed |
Carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles |
| title_sort |
carbene-catalyzed reaction of indolyl methylenemalononitriles and enals for access to complex tetrahydrocarbazoles |
| publishDate |
2021 |
| url |
https://hdl.handle.net/10356/148641 |
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1759854812357197824 |