Palladacycle-catalyzed asymmetric hydrophosphination of enones for synthesis of C*- and P*-chiral tertiary phosphines
A highly reactive and stereoselective hydrophosphination of enones catalyzed by palladacycles for the synthesis of C*- and P*-chiral tertiary phosphines has been developed. When Ph2PH was employed as the hydrophosphinating reagent, a series of C*-chiral tertiary phosphines were synthesized (C*–P bon...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2013
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| Online Access: | https://hdl.handle.net/10356/96850 http://hdl.handle.net/10220/11598 |
| _version_ | 1826115356633071616 |
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| author | Pullarkat, Sumod A. Huang, Yinhua Li, Yongxin Leung, Pak-Hing |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Pullarkat, Sumod A. Huang, Yinhua Li, Yongxin Leung, Pak-Hing |
| author_sort | Pullarkat, Sumod A. |
| collection | NTU |
| description | A highly reactive and stereoselective hydrophosphination of enones catalyzed by palladacycles for the synthesis of C*- and P*-chiral tertiary phosphines has been developed. When Ph2PH was employed as the hydrophosphinating reagent, a series of C*-chiral tertiary phosphines were synthesized (C*–P bond formation) in high yields with excellent enantioselectivities, and a single recrystallization provides access to their enantiomerically pure forms. When racemic secondary phosphines rac-R3(R4)PH were utilized, a series of tertiary phosphines containing both C*- and P*-chiral centers were generated (C*–P* bond formation) in high yields with good diastereo- and enantioselectivities. The stereoelectronic factors involved in the catalytic cycle have been revealed. |
| first_indexed | 2024-10-01T03:54:07Z |
| format | Journal Article |
| id | ntu-10356/96850 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:54:07Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | ntu-10356/968502020-03-07T12:37:09Z Palladacycle-catalyzed asymmetric hydrophosphination of enones for synthesis of C*- and P*-chiral tertiary phosphines Pullarkat, Sumod A. Huang, Yinhua Li, Yongxin Leung, Pak-Hing School of Physical and Mathematical Sciences A highly reactive and stereoselective hydrophosphination of enones catalyzed by palladacycles for the synthesis of C*- and P*-chiral tertiary phosphines has been developed. When Ph2PH was employed as the hydrophosphinating reagent, a series of C*-chiral tertiary phosphines were synthesized (C*–P bond formation) in high yields with excellent enantioselectivities, and a single recrystallization provides access to their enantiomerically pure forms. When racemic secondary phosphines rac-R3(R4)PH were utilized, a series of tertiary phosphines containing both C*- and P*-chiral centers were generated (C*–P* bond formation) in high yields with good diastereo- and enantioselectivities. The stereoelectronic factors involved in the catalytic cycle have been revealed. 2013-07-16T07:44:45Z 2019-12-06T19:35:43Z 2013-07-16T07:44:45Z 2019-12-06T19:35:43Z 2012 2012 Journal Article Huang, Y., Pullarkat, S. A., Li, Y., & Leung, P.-H. (2012). Palladacycle-Catalyzed Asymmetric Hydrophosphination of Enones for Synthesis of C*- and P*-Chiral Tertiary Phosphines. Inorganic Chemistry, 51(4), 2533-2540. https://hdl.handle.net/10356/96850 http://hdl.handle.net/10220/11598 10.1021/ic202472f en Inorganic chemistry © 2012 American Chemical Society. |
| spellingShingle | Pullarkat, Sumod A. Huang, Yinhua Li, Yongxin Leung, Pak-Hing Palladacycle-catalyzed asymmetric hydrophosphination of enones for synthesis of C*- and P*-chiral tertiary phosphines |
| title | Palladacycle-catalyzed asymmetric hydrophosphination of enones for synthesis of C*- and P*-chiral tertiary phosphines |
| title_full | Palladacycle-catalyzed asymmetric hydrophosphination of enones for synthesis of C*- and P*-chiral tertiary phosphines |
| title_fullStr | Palladacycle-catalyzed asymmetric hydrophosphination of enones for synthesis of C*- and P*-chiral tertiary phosphines |
| title_full_unstemmed | Palladacycle-catalyzed asymmetric hydrophosphination of enones for synthesis of C*- and P*-chiral tertiary phosphines |
| title_short | Palladacycle-catalyzed asymmetric hydrophosphination of enones for synthesis of C*- and P*-chiral tertiary phosphines |
| title_sort | palladacycle catalyzed asymmetric hydrophosphination of enones for synthesis of c and p chiral tertiary phosphines |
| url | https://hdl.handle.net/10356/96850 http://hdl.handle.net/10220/11598 |
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