Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules
Disclosed herein is the first carbene-organocatalyzed asymmetric addition of phosphine nucleophiles to the in situ generated α,β-unsaturated acyl azolium intermediates. Our reaction enantioselectively constructs carbon-phosphine bonds and prepares chiral phosphines with high optical purities. The ph...
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sg-ntu-dr.10356-1550582023-02-28T19:56:50Z Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules Maiti, Rakesh Yan, Jia-Lei Yang, Xing Mondal, Bivas Xu, Jun Chai, Huifang Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Asymmetric Hydrophosphination Chiral Phosphine Disclosed herein is the first carbene-organocatalyzed asymmetric addition of phosphine nucleophiles to the in situ generated α,β-unsaturated acyl azolium intermediates. Our reaction enantioselectively constructs carbon-phosphine bonds and prepares chiral phosphines with high optical purities. The phosphine products are suitable for transforming to chiral ligands or catalysts with applications in asymmetric catalysis. The diarylalkyl or trialkyl phosphine products from our catalytic reactions, air-sensitive and reactive in nature, can be trapped (and stored) in their sulfur-oxidized form for operational simplicities. Ministry of Education (MOE) National Research Foundation (NRF) Accepted version We acknowledge financial supports fromSingapore National Research Foundation under its NRFInvestigatorship (NRF-NRFI2016-06) and CompetitiveResearch Program (NRF-CRP22-2019-0002); the Ministryof Education, Singapore, under its MOE AcRF Tier 1 Award(RG7/20, RG5/19), MOE AcRF Tier 2 (MOE2019-T2-2-117),MOE AcRF Tier 3 Award (MOE2018-T3-1-003); NanyangResearch Award Grant, Chair Professorship Grant, NanyangTechnological University; the National Natural ScienceFoundation of China (21772029, 22071036, 21801051,21961006), Frontiers Science Center for Asymmetric Syn-thesis and Medicinal Molecules, Department of Education,Guizhou Province [Qianjiaohe KY number (2020)004]; The10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649);the Science and Technology Department of Guizhou Province ([2018]2802, [2019]1020); the Program of IntroducingTalents of Discipline to Universities of China (111 Program-D20023) at Guizhou University; Guizhou University ofTraditional Chinese Medicine; and Guizhou University. 2022-02-04T05:11:43Z 2022-02-04T05:11:43Z 2021 Journal Article Maiti, R., Yan, J., Yang, X., Mondal, B., Xu, J., Chai, H., Jin, Z. & Chi, R. Y. (2021). Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules. Angewandte Chemie International Edition, 60(51), 26616-26621. https://dx.doi.org/10.1002/anie.202112860 1521-3773 https://hdl.handle.net/10356/155058 10.1002/anie.202112860 34599547 2-s2.0-85118557116 51 60 26616 26621 en NRF-NRFI2016-0 NRF-CRP22-2019-0002 RG7/20 RG5/19 MOE2019-T2-2-117 MOE2018-T3-1-003 Angewandte Chemie International Edition This is the peer reviewed version of the following article: Maiti, R., Yan, J., Yang, X., Mondal, B., Xu, J., Chai, H., Jin, Z. & Chi, R. Y. (2021). Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules. Angewandte Chemie International Edition, 60(51), 26616-26621, which has been published in final form at https://doi.org/10.1002/anie.202112860. 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::Chemistry Asymmetric Hydrophosphination Chiral Phosphine Maiti, Rakesh Yan, Jia-Lei Yang, Xing Mondal, Bivas Xu, Jun Chai, Huifang Jin, Zhichao Chi, Robin Yonggui Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules |
| description |
Disclosed herein is the first carbene-organocatalyzed asymmetric addition of phosphine nucleophiles to the in situ generated α,β-unsaturated acyl azolium intermediates. Our reaction enantioselectively constructs carbon-phosphine bonds and prepares chiral phosphines with high optical purities. The phosphine products are suitable for transforming to chiral ligands or catalysts with applications in asymmetric catalysis. The diarylalkyl or trialkyl phosphine products from our catalytic reactions, air-sensitive and reactive in nature, can be trapped (and stored) in their sulfur-oxidized form for operational simplicities. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Maiti, Rakesh Yan, Jia-Lei Yang, Xing Mondal, Bivas Xu, Jun Chai, Huifang Jin, Zhichao Chi, Robin Yonggui |
| format |
Article |
| author |
Maiti, Rakesh Yan, Jia-Lei Yang, Xing Mondal, Bivas Xu, Jun Chai, Huifang Jin, Zhichao Chi, Robin Yonggui |
| author_sort |
Maiti, Rakesh |
| title |
Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules |
| title_short |
Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules |
| title_full |
Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules |
| title_fullStr |
Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules |
| title_full_unstemmed |
Carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules |
| title_sort |
carbene-catalyzed enantioselective hydrophosphination of α-bromoenals to prepare phosphine-containing chiral molecules |
| publishDate |
2022 |
| url |
https://hdl.handle.net/10356/155058 |
| _version_ |
1759857162371203072 |