Carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones
A carbene-catalyzed addition reaction between isothioureas and enals under oxidative conditions is reported. The key steps of our reactions involve the formation of two carbon–nitrogen bonds in a highly regio-selective manner. A variety of sulphur-containing 5,6-dihydropyrimidin-4-ones are obtained...
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sg-ntu-dr.10356-1482272023-02-28T19:53:34Z Carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones Maiti, Rakesh Xu, Jun Yan, Jia-Lei Mondal, Bivas Yang, Xing Chai, Huifang Hao, Lin Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Addition Reactions Catalysis A carbene-catalyzed addition reaction between isothioureas and enals under oxidative conditions is reported. The key steps of our reactions involve the formation of two carbon–nitrogen bonds in a highly regio-selective manner. A variety of sulphur-containing 5,6-dihydropyrimidin-4-ones are obtained with high optical purity. Ministry of Education (MOE) National Research Foundation (NRF) Accepted version We acknowledge the financial support from the 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), the GSK-EDB Trust Fund, Nanyang Research Award Grant, Nanyang Technological University, the National Natural Science Foundation of China (21772029, 21801051 21961006, 82360589, 81360589), 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), the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, the Guizhou Province First-Class Disciplines Project [(Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008], Guizhou University of Traditional Chinese Medicine (China), and Guizhou University. 2021-04-28T06:59:04Z 2021-04-28T06:59:04Z 2021 Journal Article Maiti, R., Xu, J., Yan, J., Mondal, B., Yang, X., Chai, H., Hao, L., Jin, Z. & Chi, R. Y. (2021). Carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones. Organic Chemistry Frontiers, 8(4), 743-747. https://dx.doi.org/10.1039/D0QO01380C 2052-4129 https://hdl.handle.net/10356/148227 10.1039/D0QO01380C 4 8 743 747 en Organic Chemistry Frontiers © 2021 Partner Organisations (The Chinese Chemical Society, Shanghai Institute of Organic Chemistry, and Royal Society of Chemistry). All rights reserved. This paper was published in Organic Chemistry Frontiers and is made available with permission of Partner Organisations (The Chinese Chemical Society, Shanghai Institute of Organic Chemistry, and Royal Society of Chemistry). application/pdf |
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Science::Chemistry Addition Reactions Catalysis Maiti, Rakesh Xu, Jun Yan, Jia-Lei Mondal, Bivas Yang, Xing Chai, Huifang Hao, Lin Jin, Zhichao Chi, Robin Yonggui Carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones |
| description |
A carbene-catalyzed addition reaction between isothioureas and enals under oxidative conditions is reported. The key steps of our reactions involve the formation of two carbon–nitrogen bonds in a highly regio-selective manner. A variety of sulphur-containing 5,6-dihydropyrimidin-4-ones are obtained with high optical purity. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Maiti, Rakesh Xu, Jun Yan, Jia-Lei Mondal, Bivas Yang, Xing Chai, Huifang Hao, Lin Jin, Zhichao Chi, Robin Yonggui |
| format |
Article |
| author |
Maiti, Rakesh Xu, Jun Yan, Jia-Lei Mondal, Bivas Yang, Xing Chai, Huifang Hao, Lin Jin, Zhichao Chi, Robin Yonggui |
| author_sort |
Maiti, Rakesh |
| title |
Carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones |
| title_short |
Carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones |
| title_full |
Carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones |
| title_fullStr |
Carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones |
| title_full_unstemmed |
Carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones |
| title_sort |
carbene-catalyzed selective addition of isothioureas to enals for access to sulphur-containing 5,6-dihyropyrimidin-4-ones |
| publishDate |
2021 |
| url |
https://hdl.handle.net/10356/148227 |
| _version_ |
1759857018992066560 |