N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality
A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC-catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C-N axial chirality with excellent optical purities. The obtained axially chi...
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sg-ntu-dr.10356-1482172023-02-28T19:21:19Z N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality Li, Tingting Mou, Chengli Qi, Puying Peng, Xiaolin Jiang, Shichun Hao, Gefei Xue, Wei Yang, Song Hao, Lin Chi, Robin Yonggui Jin, Zhichao School of Physical and Mathematical Sciences Science Atroposelective Reaction Chiral C-N Axis A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC-catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C-N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations. Ministry of Education (MOE) National Research Foundation (NRF) Accepted version We acknowledge financial support from the National Natural Science Foundation of China (21772029, 21801051, 21961006, 22071036), The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649), the Guizhou Province Returned Over- sea Student Science and Technology Activity Program [(2014)-2], the Science and Technology Department of Guizhou Province ([2018]2802, [2019]1020), 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 Guizhou Province First- Class Disciplines Project [(Yiliu Xueke Jianshe Xiangmu)- GNYL(2017)008], Guizhou University of Traditional Chi- nese Medicine, and Guizhou University (China). Singapore National Research Foundation under its NRF Investigator- ship (NRF-NRFI2016-06), the Ministry of Education, Singa- pore, 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, Nanyang Research Award Grant, Nanyang Technological University. 2021-04-29T01:49:07Z 2021-04-29T01:49:07Z 2021 Journal Article Li, T., Mou, C., Qi, P., Peng, X., Jiang, S., Hao, G., Xue, W., Yang, S., Hao, L., Chi, R. Y. & Jin, Z. (2021). N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality. Angewandte Chemie International Edition, 60(17), 9362-9367. https://dx.doi.org/10.1002/anie.202010606 1521-3773 0000-0003-3003-6437 https://hdl.handle.net/10356/148217 10.1002/anie.202010606 33527623 2-s2.0-85103032732 17 60 9362 9367 en Angewandte Chemie International Edition This is the peer reviewed version of the following article: Li, T., Mou, C., Qi, P., Peng, X., Jiang, S., Hao, G., Xue, W., Yang, S., Hao, L., Chi, R. Y. & Jin, Z. (2021). N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality. Angewandte Chemie International Edition, 60(17), 9362-9367. https://dx.doi.org/10.1002/anie.202010606, which has been published in final form at https://doi.org/10.1002/anie.202010606. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf |
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Science Atroposelective Reaction Chiral C-N Axis |
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Science Atroposelective Reaction Chiral C-N Axis Li, Tingting Mou, Chengli Qi, Puying Peng, Xiaolin Jiang, Shichun Hao, Gefei Xue, Wei Yang, Song Hao, Lin Chi, Robin Yonggui Jin, Zhichao N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality |
| description |
A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC-catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C-N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Li, Tingting Mou, Chengli Qi, Puying Peng, Xiaolin Jiang, Shichun Hao, Gefei Xue, Wei Yang, Song Hao, Lin Chi, Robin Yonggui Jin, Zhichao |
| format |
Article |
| author |
Li, Tingting Mou, Chengli Qi, Puying Peng, Xiaolin Jiang, Shichun Hao, Gefei Xue, Wei Yang, Song Hao, Lin Chi, Robin Yonggui Jin, Zhichao |
| author_sort |
Li, Tingting |
| title |
N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality |
| title_short |
N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality |
| title_full |
N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality |
| title_fullStr |
N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality |
| title_full_unstemmed |
N-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with C-N axial chirality |
| title_sort |
n-heterocyclic carbene-catalyzed atroposelective annulation for access to thiazine derivatives with c-n axial chirality |
| publishDate |
2021 |
| url |
https://hdl.handle.net/10356/148217 |
| _version_ |
1759857819899658240 |