Imidazolium ion tethered TsDPENs as efficient ligands for Iridium catalyzed asymmetric transfer hydrogenation of α-keto phosphonates in water
For the first time, an efficient method has been developed by the use of imidazolium ion tethered TsDPENs as efficient ligands for Iridium-catalyzed asymmetric transfer hydrogenation (ATH) of α-ketophosphonates in water. The reaction provided the desired product α-hydroxyphosphonates in moderate to...
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| Published in | Journal of organometallic chemistry Vol. 810; pp. 12 - 14 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier B.V
15.05.2016
Elsevier |
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| Abstract | For the first time, an efficient method has been developed by the use of imidazolium ion tethered TsDPENs as efficient ligands for Iridium-catalyzed asymmetric transfer hydrogenation (ATH) of α-ketophosphonates in water. The reaction provided the desired product α-hydroxyphosphonates in moderate to good yields (44–78%) and good to excellent enantioselectivities (up to >99% ee) under mild reaction conditions without adding any surfactants. The enantiomeric excess was determined by 13P NMR by using (−)-cinchonidine as chiral solvating agent, which is a much more convenient method than chiral HPLC.
Asymmetric transfer hydrogenation (ATH) of α-ketophosphonates in water using imidazolium ion tethered TsDPENs ligands in high to excellent enantioselectivities. [Display omitted]
•Imidazolium ion tethered TsDPENs were used as efficient ligands for ATH of α-ketophosphonates in water.•The products of α-hydroxyphosphonates were obtained in good to excellent enantioselectivity.•The reactions can be conducted under mild conditions with low loading of both catalyst and hydride donor HCO2Na. |
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| AbstractList | For the first time, an efficient method has been developed by the use of imidazolium ion tethered TsDPENs as efficient ligands for Iridium-catalyzed asymmetric transfer hydrogenation (ATH) of alpha-keto-phosphonates in water. The reaction provided the desired product alpha-hydroxyphosphonates in moderate to good yields (44-78%) and good to excellent enantioselectivities (up to >99% ee) under mild reaction conditions without adding any surfactants. The enantiomeric excess was determined by P-13 NMR by using (-)-cinchonidine as chiral solvating agent, which is a much more convenient method than chiral HPLC. (C) 2016 Elsevier B.V. All rights reserved. For the first time, an efficient method has been developed by the use of imidazolium ion tethered TsDPENs as efficient ligands for Iridium-catalyzed asymmetric transfer hydrogenation (ATH) of α-ketophosphonates in water. The reaction provided the desired product α-hydroxyphosphonates in moderate to good yields (44–78%) and good to excellent enantioselectivities (up to >99% ee) under mild reaction conditions without adding any surfactants. The enantiomeric excess was determined by 13P NMR by using (−)-cinchonidine as chiral solvating agent, which is a much more convenient method than chiral HPLC. Asymmetric transfer hydrogenation (ATH) of α-ketophosphonates in water using imidazolium ion tethered TsDPENs ligands in high to excellent enantioselectivities. [Display omitted] •Imidazolium ion tethered TsDPENs were used as efficient ligands for ATH of α-ketophosphonates in water.•The products of α-hydroxyphosphonates were obtained in good to excellent enantioselectivity.•The reactions can be conducted under mild conditions with low loading of both catalyst and hydride donor HCO2Na. |
| Author | Wang, Huigang Ni, Bukuo Sun, Mengxia Campbell, Joann Kang, Guowei |
| Author_xml | – sequence: 1 givenname: Mengxia surname: Sun fullname: Sun, Mengxia organization: Department of Chemistry, Texas A&M University-Commerce, Commerce, TX 75429-3011, USA – sequence: 2 givenname: Joann surname: Campbell fullname: Campbell, Joann organization: Department of Chemistry, Texas A&M University-Commerce, Commerce, TX 75429-3011, USA – sequence: 3 givenname: Guowei surname: Kang fullname: Kang, Guowei organization: Department of Chemistry, Texas A&M University-Commerce, Commerce, TX 75429-3011, USA – sequence: 4 givenname: Huigang surname: Wang fullname: Wang, Huigang organization: Department of Chemistry, Zhejiang Sci-Tech University, 310018, China – sequence: 5 givenname: Bukuo surname: Ni fullname: Ni, Bukuo email: bukuo.ni@tamuc.edu organization: Department of Chemistry, Texas A&M University-Commerce, Commerce, TX 75429-3011, USA |
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| Keywords | Water α-Ketophosphonates Iridium Asymmetric transfer hydrogenation GREENER ACIDS HYDROXYPHOSPHONATES ALDEHYDES MICHAEL ADDITION BETA REDUCTION KETOPHOSPHONATES alpha-Ketophosphonates HIGHLY ENANTIOSELECTIVE HYDROPHOSPHONYLATION |
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| Snippet | For the first time, an efficient method has been developed by the use of imidazolium ion tethered TsDPENs as efficient ligands for Iridium-catalyzed asymmetric... |
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| SubjectTerms | Asymmetric transfer hydrogenation Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Iridium Physical Sciences Science & Technology Water α-Ketophosphonates |
| Title | Imidazolium ion tethered TsDPENs as efficient ligands for Iridium catalyzed asymmetric transfer hydrogenation of α-keto phosphonates in water |
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