Chiral 1,2,3,4-Tetrahydro-1-naphthylamine-Derived Phosphine-Phosphoramidite Ligand (THNAPhos): Application in Highly Enantioselective Hydrogenations of Functionalized CC Bonds
We have recently reported a new chiral 1,2,3,4‐tetrahydro‐1‐naphthylamine‐derived phosphine‐phosphoramidite ligand, (Rc,Ra)‐THNAPhos, that is highly efficient in the rhodium‐catalyzed asymmetric hydrogenation of a broad range of α‐enol ester phosphonates. To further demonstrate the utility of THNAPh...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2008-06, Vol.350 (9), p.1413-1418 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Qiu, Min Hu, Xiang-Ping Wang, Dao-Yong Deng, Jun Huang, Jia-Di Yu, Sai-Bo Duan, Zheng-Chao Zheng, Zhuo |
| description | We have recently reported a new chiral 1,2,3,4‐tetrahydro‐1‐naphthylamine‐derived phosphine‐phosphoramidite ligand, (Rc,Ra)‐THNAPhos, that is highly efficient in the rhodium‐catalyzed asymmetric hydrogenation of a broad range of α‐enol ester phosphonates. To further demonstrate the utility of THNAPhos in asymmetric hydrogenation, in this paper, we describe its new application in the asymmetric hydrogenation of α‐dehydroamino acid esters, enamides, dimethyl itaconate and α‐enamido phosphonates. The results disclosed that the Rh/(Rc,Ra)‐THNAPhos complex is highly effective for the enantioselective hydrogenation of these kinds of functionalized CC olefins, affording the corresponding hydrogenation product in excellent enantioselectivities (normally over 99% ee). |
| doi_str_mv | 10.1002/adsc.200800152 |
| format | Article |
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To further demonstrate the utility of THNAPhos in asymmetric hydrogenation, in this paper, we describe its new application in the asymmetric hydrogenation of α‐dehydroamino acid esters, enamides, dimethyl itaconate and α‐enamido phosphonates. The results disclosed that the Rh/(Rc,Ra)‐THNAPhos complex is highly effective for the enantioselective hydrogenation of these kinds of functionalized CC olefins, affording the corresponding hydrogenation product in excellent enantioselectivities (normally over 99% ee).</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.200800152</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>asymmetric catalysis ; hydrogenation ; olefins ; phosphine-phosphoramidite ligand</subject><ispartof>Advanced synthesis & catalysis, 2008-06, Vol.350 (9), p.1413-1418</ispartof><rights>Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3582-2c05ab3e75c8740df03adbdd8a5c5a1e50c774641f8089d3d6bbe909d9c4d3ba3</citedby><cites>FETCH-LOGICAL-c3582-2c05ab3e75c8740df03adbdd8a5c5a1e50c774641f8089d3d6bbe909d9c4d3ba3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.200800152$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.200800152$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Qiu, Min</creatorcontrib><creatorcontrib>Hu, Xiang-Ping</creatorcontrib><creatorcontrib>Wang, Dao-Yong</creatorcontrib><creatorcontrib>Deng, Jun</creatorcontrib><creatorcontrib>Huang, Jia-Di</creatorcontrib><creatorcontrib>Yu, Sai-Bo</creatorcontrib><creatorcontrib>Duan, Zheng-Chao</creatorcontrib><creatorcontrib>Zheng, Zhuo</creatorcontrib><title>Chiral 1,2,3,4-Tetrahydro-1-naphthylamine-Derived Phosphine-Phosphoramidite Ligand (THNAPhos): Application in Highly Enantioselective Hydrogenations of Functionalized CC Bonds</title><title>Advanced synthesis & catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>We have recently reported a new chiral 1,2,3,4‐tetrahydro‐1‐naphthylamine‐derived phosphine‐phosphoramidite ligand, (Rc,Ra)‐THNAPhos, that is highly efficient in the rhodium‐catalyzed asymmetric hydrogenation of a broad range of α‐enol ester phosphonates. To further demonstrate the utility of THNAPhos in asymmetric hydrogenation, in this paper, we describe its new application in the asymmetric hydrogenation of α‐dehydroamino acid esters, enamides, dimethyl itaconate and α‐enamido phosphonates. The results disclosed that the Rh/(Rc,Ra)‐THNAPhos complex is highly effective for the enantioselective hydrogenation of these kinds of functionalized CC olefins, affording the corresponding hydrogenation product in excellent enantioselectivities (normally over 99% ee).</description><subject>asymmetric catalysis</subject><subject>hydrogenation</subject><subject>olefins</subject><subject>phosphine-phosphoramidite ligand</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNqFkUuO1DAQhiMEEsPAlrVXCKROjx9xnLBrMo-M1GqQaIQ0G8uxnY7B7QQ7PUO4DjfgAFyJK0wyQS12rFyu-r6qxR9FLxFcIgjxmVBBLjGEGYSI4kfRCUoRjROU5o-PNYVPo2chfBkRljF2Ev0qGuOFBWiBF2SRxFvde9EMyrcxip3omr4ZrNgbp-Nz7c2tVuBD04aumTpz1fpxrkyvwdrshFPg9bbcrKbZm7dg1XXWSNGb1gHjQGl2jR3AhRNubAVttezHpaCcLu60ewADaGtweXBy-ghrfoxHiz8_fxfgXetUeB49qYUN-sXf9zT6dHmxLcp4_f7qulitY0lohmMsIRUV0YzKjCVQ1ZAIVSmVCSqpQJpCyViSJqjOYJYrotKq0jnMVS4TRSpBTqNX897Ot98OOvR8b4LU1gqn20PghGCCUYJHcDmD0rcheF3zzpu98ANHkE_R8CkafoxmFPJZuDNWD_-h-er8Y_GvG8-uCb3-fnSF_8pTRhjlnzdXPLu5QXlKNrwk91Qapfg</recordid><startdate>20080609</startdate><enddate>20080609</enddate><creator>Qiu, Min</creator><creator>Hu, Xiang-Ping</creator><creator>Wang, Dao-Yong</creator><creator>Deng, Jun</creator><creator>Huang, Jia-Di</creator><creator>Yu, Sai-Bo</creator><creator>Duan, Zheng-Chao</creator><creator>Zheng, Zhuo</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20080609</creationdate><title>Chiral 1,2,3,4-Tetrahydro-1-naphthylamine-Derived Phosphine-Phosphoramidite Ligand (THNAPhos): Application in Highly Enantioselective Hydrogenations of Functionalized CC Bonds</title><author>Qiu, Min ; Hu, Xiang-Ping ; Wang, Dao-Yong ; Deng, Jun ; Huang, Jia-Di ; Yu, Sai-Bo ; Duan, Zheng-Chao ; Zheng, Zhuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3582-2c05ab3e75c8740df03adbdd8a5c5a1e50c774641f8089d3d6bbe909d9c4d3ba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>asymmetric catalysis</topic><topic>hydrogenation</topic><topic>olefins</topic><topic>phosphine-phosphoramidite ligand</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qiu, Min</creatorcontrib><creatorcontrib>Hu, Xiang-Ping</creatorcontrib><creatorcontrib>Wang, Dao-Yong</creatorcontrib><creatorcontrib>Deng, Jun</creatorcontrib><creatorcontrib>Huang, Jia-Di</creatorcontrib><creatorcontrib>Yu, Sai-Bo</creatorcontrib><creatorcontrib>Duan, Zheng-Chao</creatorcontrib><creatorcontrib>Zheng, Zhuo</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qiu, Min</au><au>Hu, Xiang-Ping</au><au>Wang, Dao-Yong</au><au>Deng, Jun</au><au>Huang, Jia-Di</au><au>Yu, Sai-Bo</au><au>Duan, Zheng-Chao</au><au>Zheng, Zhuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral 1,2,3,4-Tetrahydro-1-naphthylamine-Derived Phosphine-Phosphoramidite Ligand (THNAPhos): Application in Highly Enantioselective Hydrogenations of Functionalized CC Bonds</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2008-06-09</date><risdate>2008</risdate><volume>350</volume><issue>9</issue><spage>1413</spage><epage>1418</epage><pages>1413-1418</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>We have recently reported a new chiral 1,2,3,4‐tetrahydro‐1‐naphthylamine‐derived phosphine‐phosphoramidite ligand, (Rc,Ra)‐THNAPhos, that is highly efficient in the rhodium‐catalyzed asymmetric hydrogenation of a broad range of α‐enol ester phosphonates. To further demonstrate the utility of THNAPhos in asymmetric hydrogenation, in this paper, we describe its new application in the asymmetric hydrogenation of α‐dehydroamino acid esters, enamides, dimethyl itaconate and α‐enamido phosphonates. The results disclosed that the Rh/(Rc,Ra)‐THNAPhos complex is highly effective for the enantioselective hydrogenation of these kinds of functionalized CC olefins, affording the corresponding hydrogenation product in excellent enantioselectivities (normally over 99% ee).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.200800152</doi><tpages>6</tpages></addata></record> |
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| subjects | asymmetric catalysis hydrogenation olefins phosphine-phosphoramidite ligand |
| title | Chiral 1,2,3,4-Tetrahydro-1-naphthylamine-Derived Phosphine-Phosphoramidite Ligand (THNAPhos): Application in Highly Enantioselective Hydrogenations of Functionalized CC Bonds |
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