Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates
Asymmetric arylation of γ,δ-unsaturated β-ketophosphonates with arylboronic acids is reported. By using the (R)-diene* ligated rhodium(I) chloride complex as a catalyst under none basic conditions, the corresponding β-ketophosphonates bearing a δ-chiral center were obtained in high yields (up to 99%...
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sg-ntu-dr.10356-1396572020-05-21T01:02:47Z Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates Yin, Long Zhang, Dewei Xing, Junhao Wang, Yuhan Wu, Changhui Lu, Tao Chen, Yadong Hayashi, Tamio Dou, Xiaowei School of Physical and Mathematical Sciences Science::Chemistry Stereoselectivity Catalysts Asymmetric arylation of γ,δ-unsaturated β-ketophosphonates with arylboronic acids is reported. By using the (R)-diene* ligated rhodium(I) chloride complex as a catalyst under none basic conditions, the corresponding β-ketophosphonates bearing a δ-chiral center were obtained in high yields (up to 99%) with good to excellent enantioselectivities (up to >99% ee). The enantioenriched products can be readily converted to diverse chiral β′-aryl enones by the Horner–Wadsworth–Emmons reaction. MOE (Min. of Education, S’pore) 2020-05-21T01:02:47Z 2020-05-21T01:02:47Z 2018 Journal Article Yin, L., Zhang, D., Xing, J., Wang, Y., Wu, C., Lu, T., . . . Dou, X. (2018). Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates. The Journal of Organic Chemistry, 83(10), 5869-5875. doi:10.1021/acs.joc.8b00952 0022-3263 https://hdl.handle.net/10356/139657 10.1021/acs.joc.8b00952 29715022 2-s2.0-85046540338 10 83 5869 5875 en The Journal of Organic Chemistry © 2018 American Chemical Society. All rights reserved. |
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Science::Chemistry Stereoselectivity Catalysts Yin, Long Zhang, Dewei Xing, Junhao Wang, Yuhan Wu, Changhui Lu, Tao Chen, Yadong Hayashi, Tamio Dou, Xiaowei Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates |
| description |
Asymmetric arylation of γ,δ-unsaturated β-ketophosphonates with arylboronic acids is reported. By using the (R)-diene* ligated rhodium(I) chloride complex as a catalyst under none basic conditions, the corresponding β-ketophosphonates bearing a δ-chiral center were obtained in high yields (up to 99%) with good to excellent enantioselectivities (up to >99% ee). The enantioenriched products can be readily converted to diverse chiral β′-aryl enones by the Horner–Wadsworth–Emmons reaction. |
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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Yin, Long Zhang, Dewei Xing, Junhao Wang, Yuhan Wu, Changhui Lu, Tao Chen, Yadong Hayashi, Tamio Dou, Xiaowei |
| format |
Article |
| author |
Yin, Long Zhang, Dewei Xing, Junhao Wang, Yuhan Wu, Changhui Lu, Tao Chen, Yadong Hayashi, Tamio Dou, Xiaowei |
| author_sort |
Yin, Long |
| title |
Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates |
| title_short |
Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates |
| title_full |
Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates |
| title_fullStr |
Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates |
| title_full_unstemmed |
Access to chiral HWE reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates |
| title_sort |
access to chiral hwe reagents by rhodium-catalyzed asymmetric arylation of γ,δ-unsaturated β-ketophosphonates |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/139657 |
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1681057118536335360 |