Asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution
We have developed a catalytic method using chiral N-heterocyclic carbene (NHC) as the sole organic catalyst to synthesize planar chiral carbonitriles asymmetrically, resulting in optically pure, multifunctional compounds. The method demonstrates remarkable tolerance toward diverse substituents and s...
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sg-ntu-dr.10356-1743602024-04-05T15:31:55Z Asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution Lv, Ya Mou, Chengli Liu, Qian Shu, Liangzhen Cai, Yuanlin Lv, Xiaokang Jin, Zhichao Chi, Robin Yonggui School of Chemistry, Chemical Engineering and Biotechnology Chemistry Amine Carbene We have developed a catalytic method using chiral N-heterocyclic carbene (NHC) as the sole organic catalyst to synthesize planar chiral carbonitriles asymmetrically, resulting in optically pure, multifunctional compounds. The method demonstrates remarkable tolerance toward diverse substituents and substitution patterns through kinetic resolution (KR) or desymmetrization processes. The resulting optically pure planar chiral products hold significant potential for applications in asymmetric synthesis and antibacterial pesticide development. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) Submitted/Accepted version We acknowledge funding supports from the National Key Research and Development Program of China (2022YFD-1700300); National Natural Science Foundation of China (21732002, 21961006, 32172459, 22061007, 22071036), Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY number (2020)004] ,the Science and Technology Department of Guizhou Province (Qianke-hejichu-ZK[2021]Key033), Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, Guizhou University of Traditional Chinese Medicine, and Guizhou University (China). Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016-06) and Competitive Research Program (NRF-CRP22-2019-0002); the Singapore Ministry of Education under its MOE AcRF Tier 1 Award (RG7/20, RG5/19), MOE AcRF Tier2 Award (MOE2019-T2-2-117), and MOE AcRF Tier 3 Award (MOE2018-T3-1-003), and Nanyang Technological University. 2024-04-01T01:51:42Z 2024-04-01T01:51:42Z 2024 Journal Article Lv, Y., Mou, C., Liu, Q., Shu, L., Cai, Y., Lv, X., Jin, Z. & Chi, R. Y. (2024). Asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution. Organic Letters, 26(8), 1584-1588. https://dx.doi.org/10.1021/acs.orglett.3c04342 1523-7060 https://hdl.handle.net/10356/174360 10.1021/acs.orglett.3c04342 26 2-s2.0-85186090124 8 26 1584 1588 en NRF-NRFI2016-06 NRF-CRP22-2019-0002 RG7/20 RG5/19 MOE2019-T2-2-117 MOE2018-T3-1-003 Organic Letters © 2024 American Chemical Society. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1021/acs.orglett.3c04342. application/pdf |
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Chemistry Amine Carbene |
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Chemistry Amine Carbene Lv, Ya Mou, Chengli Liu, Qian Shu, Liangzhen Cai, Yuanlin Lv, Xiaokang Jin, Zhichao Chi, Robin Yonggui Asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution |
| description |
We have developed a catalytic method using chiral N-heterocyclic carbene (NHC) as the sole organic catalyst to synthesize planar chiral carbonitriles asymmetrically, resulting in optically pure, multifunctional compounds. The method demonstrates remarkable tolerance toward diverse substituents and substitution patterns through kinetic resolution (KR) or desymmetrization processes. The resulting optically pure planar chiral products hold significant potential for applications in asymmetric synthesis and antibacterial pesticide development. |
| author2 |
School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet |
School of Chemistry, Chemical Engineering and Biotechnology Lv, Ya Mou, Chengli Liu, Qian Shu, Liangzhen Cai, Yuanlin Lv, Xiaokang Jin, Zhichao Chi, Robin Yonggui |
| format |
Article |
| author |
Lv, Ya Mou, Chengli Liu, Qian Shu, Liangzhen Cai, Yuanlin Lv, Xiaokang Jin, Zhichao Chi, Robin Yonggui |
| author_sort |
Lv, Ya |
| title |
Asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution |
| title_short |
Asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution |
| title_full |
Asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution |
| title_fullStr |
Asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution |
| title_full_unstemmed |
Asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution |
| title_sort |
asymmetric synthesis of planar chiral carbonitriles and amines via carbene-catalyzed kinetic resolution |
| publishDate |
2024 |
| url |
https://hdl.handle.net/10356/174360 |
| _version_ |
1814047361468465152 |