Enantioselective Synthesis of Chiral 3‐Substituted‐3‐silylpropionic Esters via Rhodium/Bisphosphine‐Thiourea‐Catalyzed Asymmetric Hydrogenation
We have successfully developed the asymmetric hydrogenation of β‐silyl‐α,β‐unsaturated esters to prepare chiral 3‐substituted‐3‐silylpropionic ester products catalyzed by rhodium/bisphosphine‐thiourea (ZhaoPhos) with excellent results (up to 97% yield, >99% ee, 1500 TON). Moreover, our hydrogenat...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2017-08, Vol.359 (15), p.2585-2589 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Zhang, Zongpeng Han, Zhengyu Gu, Guoxian Dong, Xiu‐Qin Zhang, Xumu |
| description | We have successfully developed the asymmetric hydrogenation of β‐silyl‐α,β‐unsaturated esters to prepare chiral 3‐substituted‐3‐silylpropionic ester products catalyzed by rhodium/bisphosphine‐thiourea (ZhaoPhos) with excellent results (up to 97% yield, >99% ee, 1500 TON). Moreover, our hydrogenation products can be efficiently converted to other important organic molecules, such as chiral ethyl (R)‐3‐hydroxy‐3‐phenylpropanoate or (R)‐3‐[dimethyl(phenyl)silyl]‐3‐phenylpropanoic acid. |
| doi_str_mv | 10.1002/adsc.201700355 |
| format | Article |
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Moreover, our hydrogenation products can be efficiently converted to other important organic molecules, such as chiral ethyl (R)‐3‐hydroxy‐3‐phenylpropanoate or (R)‐3‐[dimethyl(phenyl)silyl]‐3‐phenylpropanoic acid.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201700355</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>asymmetric hydrogenation ; bisphosphine-thiourea ligand ; Chemical synthesis ; chiral silicon compounds ; enantioselectivity ; Esters ; Hydrogenation ; Organic chemistry ; Rhodium ; β-silyl-α,β-unsaturated esters</subject><ispartof>Advanced synthesis & catalysis, 2017-08, Vol.359 (15), p.2585-2589</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3545-304dd6ca60d3e8fb869d608641b401308e7364272be27f4e2b3f5b958839cf413</citedby><cites>FETCH-LOGICAL-c3545-304dd6ca60d3e8fb869d608641b401308e7364272be27f4e2b3f5b958839cf413</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.201700355$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201700355$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Zhang, Zongpeng</creatorcontrib><creatorcontrib>Han, Zhengyu</creatorcontrib><creatorcontrib>Gu, Guoxian</creatorcontrib><creatorcontrib>Dong, Xiu‐Qin</creatorcontrib><creatorcontrib>Zhang, Xumu</creatorcontrib><title>Enantioselective Synthesis of Chiral 3‐Substituted‐3‐silylpropionic Esters via Rhodium/Bisphosphine‐Thiourea‐Catalyzed Asymmetric Hydrogenation</title><title>Advanced synthesis & catalysis</title><description>We have successfully developed the asymmetric hydrogenation of β‐silyl‐α,β‐unsaturated esters to prepare chiral 3‐substituted‐3‐silylpropionic ester products catalyzed by rhodium/bisphosphine‐thiourea (ZhaoPhos) with excellent results (up to 97% yield, >99% ee, 1500 TON). Moreover, our hydrogenation products can be efficiently converted to other important organic molecules, such as chiral ethyl (R)‐3‐hydroxy‐3‐phenylpropanoate or (R)‐3‐[dimethyl(phenyl)silyl]‐3‐phenylpropanoic acid.</description><subject>asymmetric hydrogenation</subject><subject>bisphosphine-thiourea ligand</subject><subject>Chemical synthesis</subject><subject>chiral silicon compounds</subject><subject>enantioselectivity</subject><subject>Esters</subject><subject>Hydrogenation</subject><subject>Organic chemistry</subject><subject>Rhodium</subject><subject>β-silyl-α,β-unsaturated esters</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFUMtOwzAQjBBIlMKVcyTObf3K61hCoUiVkGg5R068Ia6SONgOKJz4BK78Hl-Cq6Jy5LDah2Zmd8fzLjGaYoTIjAtTTAnCEUI0CI68EQ5xMGE4TI4PdYBOvTNjtsjB4igaeV-LlrdWKgM1FFa-gr8eWluBkcZXpZ9WUvPap98fn-s-N1ba3oJw3W5iZD3UnVadVK0s_IWxoI3_Krn_WCkh-2Z2LU1XKReyBUfYVFL1GrgrU255PbyD8OdmaBqw2iksB6HVM7TcHdSeeyclrw1c_Oax93S72KTLyerh7j6dryYFDVgwoYgJERY8RIJCXOZxmIgQxSHDOUOYohgiGjISkRxIVDIgOS2DPAnimCZFyTAde1d7XffJSw_GZlt3ZOtWZjghTsdZRRxqukcVWhmjocw6LRuuhwyjbGd_trM_O9jvCMme8CZrGP5BZ_ObdfrH_QHXlpG9</recordid><startdate>20170807</startdate><enddate>20170807</enddate><creator>Zhang, Zongpeng</creator><creator>Han, Zhengyu</creator><creator>Gu, Guoxian</creator><creator>Dong, Xiu‐Qin</creator><creator>Zhang, Xumu</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20170807</creationdate><title>Enantioselective Synthesis of Chiral 3‐Substituted‐3‐silylpropionic Esters via Rhodium/Bisphosphine‐Thiourea‐Catalyzed Asymmetric Hydrogenation</title><author>Zhang, Zongpeng ; Han, Zhengyu ; Gu, Guoxian ; Dong, Xiu‐Qin ; Zhang, Xumu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3545-304dd6ca60d3e8fb869d608641b401308e7364272be27f4e2b3f5b958839cf413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>asymmetric hydrogenation</topic><topic>bisphosphine-thiourea ligand</topic><topic>Chemical synthesis</topic><topic>chiral silicon compounds</topic><topic>enantioselectivity</topic><topic>Esters</topic><topic>Hydrogenation</topic><topic>Organic chemistry</topic><topic>Rhodium</topic><topic>β-silyl-α,β-unsaturated esters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zongpeng</creatorcontrib><creatorcontrib>Han, Zhengyu</creatorcontrib><creatorcontrib>Gu, Guoxian</creatorcontrib><creatorcontrib>Dong, Xiu‐Qin</creatorcontrib><creatorcontrib>Zhang, Xumu</creatorcontrib><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>Zhang, Zongpeng</au><au>Han, Zhengyu</au><au>Gu, Guoxian</au><au>Dong, Xiu‐Qin</au><au>Zhang, Xumu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of Chiral 3‐Substituted‐3‐silylpropionic Esters via Rhodium/Bisphosphine‐Thiourea‐Catalyzed Asymmetric Hydrogenation</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2017-08-07</date><risdate>2017</risdate><volume>359</volume><issue>15</issue><spage>2585</spage><epage>2589</epage><pages>2585-2589</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>We have successfully developed the asymmetric hydrogenation of β‐silyl‐α,β‐unsaturated esters to prepare chiral 3‐substituted‐3‐silylpropionic ester products catalyzed by rhodium/bisphosphine‐thiourea (ZhaoPhos) with excellent results (up to 97% yield, >99% ee, 1500 TON). Moreover, our hydrogenation products can be efficiently converted to other important organic molecules, such as chiral ethyl (R)‐3‐hydroxy‐3‐phenylpropanoate or (R)‐3‐[dimethyl(phenyl)silyl]‐3‐phenylpropanoic acid.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201700355</doi><tpages>5</tpages></addata></record> |
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| subjects | asymmetric hydrogenation bisphosphine-thiourea ligand Chemical synthesis chiral silicon compounds enantioselectivity Esters Hydrogenation Organic chemistry Rhodium β-silyl-α,β-unsaturated esters |
| title | Enantioselective Synthesis of Chiral 3‐Substituted‐3‐silylpropionic Esters via Rhodium/Bisphosphine‐Thiourea‐Catalyzed Asymmetric Hydrogenation |
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