Carbene-catalyzed atroposelective annulation and desymmetrization of urazoles
An NHC-catalyzed atroposelective reaction between ynals and urazoles is disclosed. The reaction establishes a chiral C-N axis via an atroposelective [3 + 2] annulation/desymmetrization process. Our reaction allows efficient access to axially chiral and heteroatom-rich urazole derivatives with potent...
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sg-ntu-dr.10356-1550712022-02-22T08:12:17Z Carbene-catalyzed atroposelective annulation and desymmetrization of urazoles Jin, Jiamiao Huang, Xuan Xu, Jun Li, Tingting Peng, Xiaolin Zhu, Xun Zhang, Junmin Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Chirality Chemical Reactions An NHC-catalyzed atroposelective reaction between ynals and urazoles is disclosed. The reaction establishes a chiral C-N axis via an atroposelective [3 + 2] annulation/desymmetrization process. Our reaction allows efficient access to axially chiral and heteroatom-rich urazole derivatives with potential applications in bioactive molecules and catalysis. Agency for Science, Technology and Research (A*STAR) Economic Development Board (EDB) Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) We acknowledge financial support from the National Natural Science Foundation of China (21772029, 21801051, 21961006, 22001173), The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649), the Guizhou Province Returned Oversea Student Science and Technology Activity Program [(2014)-2], the Science and Technology Department of Guizhou Province ([2018]2802, [2019]1020, Qiankehejichu-ZK[2021]Key033), the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY (2020)004], the Basic and Applied Research Foundation of Guangdong Province (2019A1515110906), the Guizhou Province FirstClass Disciplines Project [(Yiliu Xueke Jianshe Xiangmu)- GNYL(2017)008], Guizhou University of Traditional Chinese Medicine, and Guizhou University (China). Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016-06), the Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG108/16, RG5/19, RG1/18), MOE AcRF Tier 3 Award (MOE2018-T3-1-003), the Agency for Science, Technology and Research (A*STAR) under its A*STAR AME IRG Award (A1783c0008, A1783c0010), GSK-EDB Trust Fund, and Nanyang Research Award Grant, Nanyang Technological University. 2022-02-22T08:12:17Z 2022-02-22T08:12:17Z 2021 Journal Article Jin, J., Huang, X., Xu, J., Li, T., Peng, X., Zhu, X., Zhang, J., Jin, Z. & Chi, R. Y. (2021). Carbene-catalyzed atroposelective annulation and desymmetrization of urazoles. Organic Letters, 23(10), 3991-3996. https://dx.doi.org/10.1021/acs.orglett.1c01191 1523-7060 https://hdl.handle.net/10356/155071 10.1021/acs.orglett.1c01191 33979174 2-s2.0-85106385909 10 23 3991 3996 en NRF-NRFI2016-06 RG108/16 RG5/19 RG1/18 MOE2018-T3-1-003 A1783c0008 A1783c0010 Organic Letters © 2021 American Chemical Society. All rights reserved. |
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Science::Chemistry Chirality Chemical Reactions Jin, Jiamiao Huang, Xuan Xu, Jun Li, Tingting Peng, Xiaolin Zhu, Xun Zhang, Junmin Jin, Zhichao Chi, Robin Yonggui Carbene-catalyzed atroposelective annulation and desymmetrization of urazoles |
| description |
An NHC-catalyzed atroposelective reaction between ynals and urazoles is disclosed. The reaction establishes a chiral C-N axis via an atroposelective [3 + 2] annulation/desymmetrization process. Our reaction allows efficient access to axially chiral and heteroatom-rich urazole derivatives with potential applications in bioactive molecules and catalysis. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Jin, Jiamiao Huang, Xuan Xu, Jun Li, Tingting Peng, Xiaolin Zhu, Xun Zhang, Junmin Jin, Zhichao Chi, Robin Yonggui |
| format |
Article |
| author |
Jin, Jiamiao Huang, Xuan Xu, Jun Li, Tingting Peng, Xiaolin Zhu, Xun Zhang, Junmin Jin, Zhichao Chi, Robin Yonggui |
| author_sort |
Jin, Jiamiao |
| title |
Carbene-catalyzed atroposelective annulation and desymmetrization of urazoles |
| title_short |
Carbene-catalyzed atroposelective annulation and desymmetrization of urazoles |
| title_full |
Carbene-catalyzed atroposelective annulation and desymmetrization of urazoles |
| title_fullStr |
Carbene-catalyzed atroposelective annulation and desymmetrization of urazoles |
| title_full_unstemmed |
Carbene-catalyzed atroposelective annulation and desymmetrization of urazoles |
| title_sort |
carbene-catalyzed atroposelective annulation and desymmetrization of urazoles |
| publishDate |
2022 |
| url |
https://hdl.handle.net/10356/155071 |
| _version_ |
1725985589594947584 |