Remarkably Diastereoselective Synthesis of a Chiral Biphenyl Diphosphine Ligand and Its Application in Asymmetric Hydrogenation
Essentially complete atropdiastereoselectivity was realized in the preparation of biaryl diphosphine dioxide by asymmetric intramolecular Ullmann coupling and oxidative coupling with central-to-axial chirality transfer. A bridged C2-symmetric biphenyl phosphine ligand possessing additional chiral ce...
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| Veröffentlicht in: | Proceedings of the National Academy of Sciences - PNAS 2004-04, Vol.101 (16), p.5815-5820 |
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| container_title | Proceedings of the National Academy of Sciences - PNAS |
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| creator | Qiu, Liqin Wu, Jing Chan, Shusun Terry T.-L. Au-Yeung Ji, Jian-Xin Guo, Rongwei Pai, Cheng-Chao Zhou, Zhongyuan Li, Xingshu Fan, Qing-Hua Albert S. C. Chan Halpern, Jack |
| description | Essentially complete atropdiastereoselectivity was realized in the preparation of biaryl diphosphine dioxide by asymmetric intramolecular Ullmann coupling and oxidative coupling with central-to-axial chirality transfer. A bridged C2-symmetric biphenyl phosphine ligand possessing additional chiral centers on the linking unit of the biphenyl groups was synthesized. No resolution step was required for the preparation of the enantiomerically pure chiral ligand. These findings offer a general and practical tool for the development of previously uninvestigated atropdiastereomeric biaryl phosphine ligands. The diphosphine ligand was found to be highly effective in the asymmetric hydrogenation of α- and β- ketoesters, 2-(6′-methoxy-2′-naphthyl)propenoic acid, β-(acylamino)acrylates, and enol acetates. |
| doi_str_mv | 10.1073/pnas.0307774101 |
| format | Article |
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The diphosphine ligand was found to be highly effective in the asymmetric hydrogenation of α- and β- ketoesters, 2-(6′-methoxy-2′-naphthyl)propenoic acid, β-(acylamino)acrylates, and enol acetates.</description><identifier>ISSN: 0027-8424</identifier><identifier>EISSN: 1091-6490</identifier><identifier>DOI: 10.1073/pnas.0307774101</identifier><identifier>PMID: 15067137</identifier><language>eng</language><publisher>United States: National Academy of Sciences</publisher><subject>Acetates ; Asymmetric Catalysis Special Feature Part II ; Chirality ; Dioxides ; Hydrogenation ; Ligands ; Lithium ; Organic chemistry ; Phosphines ; Physical Sciences ; Room temperature ; Solvents ; Tetrahedrons</subject><ispartof>Proceedings of the National Academy of Sciences - PNAS, 2004-04, Vol.101 (16), p.5815-5820</ispartof><rights>Copyright 1993/2004 The National Academy of Sciences of the United States of America</rights><rights>Copyright National Academy of Sciences Apr 20, 2004</rights><rights>Copyright © 2004, The National Academy of Sciences 2004</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c495t-e574c72bd8a3709a8812d3124de0118e516612028c389ab9ad234a7d7f072f223</citedby><cites>FETCH-LOGICAL-c495t-e574c72bd8a3709a8812d3124de0118e516612028c389ab9ad234a7d7f072f223</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://www.pnas.org/content/101/16.cover.gif</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/3371919$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/3371919$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>230,314,723,776,780,799,881,27901,27902,53766,53768,57992,58225</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15067137$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Qiu, Liqin</creatorcontrib><creatorcontrib>Wu, Jing</creatorcontrib><creatorcontrib>Chan, Shusun</creatorcontrib><creatorcontrib>Terry T.-L. 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A bridged C2-symmetric biphenyl phosphine ligand possessing additional chiral centers on the linking unit of the biphenyl groups was synthesized. No resolution step was required for the preparation of the enantiomerically pure chiral ligand. These findings offer a general and practical tool for the development of previously uninvestigated atropdiastereomeric biaryl phosphine ligands. The diphosphine ligand was found to be highly effective in the asymmetric hydrogenation of α- and β- ketoesters, 2-(6′-methoxy-2′-naphthyl)propenoic acid, β-(acylamino)acrylates, and enol acetates.</description><subject>Acetates</subject><subject>Asymmetric Catalysis Special Feature Part II</subject><subject>Chirality</subject><subject>Dioxides</subject><subject>Hydrogenation</subject><subject>Ligands</subject><subject>Lithium</subject><subject>Organic chemistry</subject><subject>Phosphines</subject><subject>Physical Sciences</subject><subject>Room temperature</subject><subject>Solvents</subject><subject>Tetrahedrons</subject><issn>0027-8424</issn><issn>1091-6490</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNp9kb2P1DAQxSME4paDmgaBRYFocuexkzguKJbl405aCYmP2vImk42XrJ2znROp-NdJ2NUtUFCMppjfm5mnlyRPgV4AFfyytzpcUE6FEBlQuJcsgEpIi0zS-8mCUibSMmPZWfIohB2lVOYlfZicQU4LAVwskp-fca_9d73pRvLO6BDRowvYYRXNLZIvo40tBhOIa4gmq9Z43ZG3pm_Rjt2k6FsX-tZYJGuz1bYmc13HQJZ935lKR-MsMZYsw7jfY_SmIldj7d0W7e_Z4-RBo7uAT479PPn24f3X1VW6_vTxerVcp1Um85hiLrJKsE1dai6o1GUJrObAshopQIk5FAUwysqKl1JvpK4Zz7SoRUMFaxjj58mbw95-2OyxrtDGyYnqvZnsj8ppo_6eWNOqrbtVXOZSwqR_ddR7dzNgiGpvQoVdpy26ISgBZV5wPh96-Q-4c4O3kzfFKPAsZ1xO0OUBqrwLwWNz9whQNQer5mDVKdhJ8fzP_0_8MckJeHEEZuVpHSgoVF5CPhGv_0-oZui6iD_ihD47oLsQnb9jORcgQfJfFzbCiA</recordid><startdate>20040420</startdate><enddate>20040420</enddate><creator>Qiu, Liqin</creator><creator>Wu, Jing</creator><creator>Chan, Shusun</creator><creator>Terry T.-L. 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| source | Jstor Complete Legacy; PubMed Central; Alma/SFX Local Collection; Free Full-Text Journals in Chemistry |
| subjects | Acetates Asymmetric Catalysis Special Feature Part II Chirality Dioxides Hydrogenation Ligands Lithium Organic chemistry Phosphines Physical Sciences Room temperature Solvents Tetrahedrons |
| title | Remarkably Diastereoselective Synthesis of a Chiral Biphenyl Diphosphine Ligand and Its Application in Asymmetric Hydrogenation |
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