Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation
A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regeneration of the DHPD under the mild condition. The...
Gespeichert in:
| Veröffentlicht in: | Journal of the American Chemical Society 2012-02, Vol.134 (4), p.2442-2448 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2448 |
|---|---|
| container_issue | 4 |
| container_start_page | 2442 |
| container_title | Journal of the American Chemical Society |
| container_volume | 134 |
| creator | Chen, Qing-An Gao, Kai Duan, Ying Ye, Zhi-Shi Shi, Lei Yang, Yan Zhou, Yong-Gui |
| description | A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regeneration of the DHPD under the mild condition. Therefore, the substrate scope is not limited in benzoxazinones; the biomimetic asymmetric hydrogenation of benzoxazines, quinoxalines, and quinolines also gives excellent activities and enantioselectivities. Meanwhile, an unexpected reversal of enantioselectivity was observed between the reactions promoted by the different NAD(P)H models, which is ascribed to the different hydride transfer pathway. |
| doi_str_mv | 10.1021/ja211684v |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_919950345</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>919950345</sourcerecordid><originalsourceid>FETCH-LOGICAL-a415t-6eaf610a9635c65d8565185c1e2c42b135425deebab5a3d9bc5cd007b0652e4f3</originalsourceid><addsrcrecordid>eNptkEFPwjAUxxujUUQPfgHTi1EO07Zb6-YNAcUE0Rg9L137JiXbiu3Q8O0tATl5ev-X_N4veX-Ezii5poTRm7lklIo0-d5DHcoZiThlYh91CCEsuk1FfISOvZ-HNWEpPURHjLE4C2QHmaGZrbSzixk0smlnzmjTwB3u4yn8YNloPJLeVCv8Bp_QgJNFBXjaH1699sb42WqocGkdvje2NjW0RuG-X9UhuRDHa3M4k62xzQk6KGXl4XQ7u-jjYfQ-GEeTl8enQX8SyYTyNhIgS0GJzETMleA65YLTlCsKTCWsoDFPGNcAhSy4jHVWKK40IbcFEZxBUsZddLnxLpz9WoJv89p4BVUlG7BLn2c0yziJEx7I3oZUznrvoMwXztTSrXJK8nWx-a7YwJ5vrcuiBr0j_5oMwMUGkMrnc7t0TXjyH9Ev_nB-8g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>919950345</pqid></control><display><type>article</type><title>Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Chen, Qing-An ; Gao, Kai ; Duan, Ying ; Ye, Zhi-Shi ; Shi, Lei ; Yang, Yan ; Zhou, Yong-Gui</creator><creatorcontrib>Chen, Qing-An ; Gao, Kai ; Duan, Ying ; Ye, Zhi-Shi ; Shi, Lei ; Yang, Yan ; Zhou, Yong-Gui</creatorcontrib><description>A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regeneration of the DHPD under the mild condition. Therefore, the substrate scope is not limited in benzoxazinones; the biomimetic asymmetric hydrogenation of benzoxazines, quinoxalines, and quinolines also gives excellent activities and enantioselectivities. Meanwhile, an unexpected reversal of enantioselectivity was observed between the reactions promoted by the different NAD(P)H models, which is ascribed to the different hydride transfer pathway.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja211684v</identifier><identifier>PMID: 22239152</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Biomimetic Materials - chemical synthesis ; Biomimetic Materials - chemistry ; Hydrocarbons, Aromatic - chemical synthesis ; Hydrocarbons, Aromatic - chemistry ; Hydrogen - chemistry ; Hydrogenation ; Imines - chemical synthesis ; Imines - chemistry ; Models, Molecular ; Molecular Structure ; NADP - chemistry ; Phenanthridines - chemical synthesis ; Phenanthridines - chemistry ; Stereoisomerism</subject><ispartof>Journal of the American Chemical Society, 2012-02, Vol.134 (4), p.2442-2448</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2012 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a415t-6eaf610a9635c65d8565185c1e2c42b135425deebab5a3d9bc5cd007b0652e4f3</citedby><cites>FETCH-LOGICAL-a415t-6eaf610a9635c65d8565185c1e2c42b135425deebab5a3d9bc5cd007b0652e4f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja211684v$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja211684v$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22239152$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Qing-An</creatorcontrib><creatorcontrib>Gao, Kai</creatorcontrib><creatorcontrib>Duan, Ying</creatorcontrib><creatorcontrib>Ye, Zhi-Shi</creatorcontrib><creatorcontrib>Shi, Lei</creatorcontrib><creatorcontrib>Yang, Yan</creatorcontrib><creatorcontrib>Zhou, Yong-Gui</creatorcontrib><title>Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regeneration of the DHPD under the mild condition. Therefore, the substrate scope is not limited in benzoxazinones; the biomimetic asymmetric hydrogenation of benzoxazines, quinoxalines, and quinolines also gives excellent activities and enantioselectivities. Meanwhile, an unexpected reversal of enantioselectivity was observed between the reactions promoted by the different NAD(P)H models, which is ascribed to the different hydride transfer pathway.</description><subject>Biomimetic Materials - chemical synthesis</subject><subject>Biomimetic Materials - chemistry</subject><subject>Hydrocarbons, Aromatic - chemical synthesis</subject><subject>Hydrocarbons, Aromatic - chemistry</subject><subject>Hydrogen - chemistry</subject><subject>Hydrogenation</subject><subject>Imines - chemical synthesis</subject><subject>Imines - chemistry</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>NADP - chemistry</subject><subject>Phenanthridines - chemical synthesis</subject><subject>Phenanthridines - chemistry</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEFPwjAUxxujUUQPfgHTi1EO07Zb6-YNAcUE0Rg9L137JiXbiu3Q8O0tATl5ev-X_N4veX-Ezii5poTRm7lklIo0-d5DHcoZiThlYh91CCEsuk1FfISOvZ-HNWEpPURHjLE4C2QHmaGZrbSzixk0smlnzmjTwB3u4yn8YNloPJLeVCv8Bp_QgJNFBXjaH1699sb42WqocGkdvje2NjW0RuG-X9UhuRDHa3M4k62xzQk6KGXl4XQ7u-jjYfQ-GEeTl8enQX8SyYTyNhIgS0GJzETMleA65YLTlCsKTCWsoDFPGNcAhSy4jHVWKK40IbcFEZxBUsZddLnxLpz9WoJv89p4BVUlG7BLn2c0yziJEx7I3oZUznrvoMwXztTSrXJK8nWx-a7YwJ5vrcuiBr0j_5oMwMUGkMrnc7t0TXjyH9Ev_nB-8g</recordid><startdate>20120201</startdate><enddate>20120201</enddate><creator>Chen, Qing-An</creator><creator>Gao, Kai</creator><creator>Duan, Ying</creator><creator>Ye, Zhi-Shi</creator><creator>Shi, Lei</creator><creator>Yang, Yan</creator><creator>Zhou, Yong-Gui</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20120201</creationdate><title>Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation</title><author>Chen, Qing-An ; Gao, Kai ; Duan, Ying ; Ye, Zhi-Shi ; Shi, Lei ; Yang, Yan ; Zhou, Yong-Gui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a415t-6eaf610a9635c65d8565185c1e2c42b135425deebab5a3d9bc5cd007b0652e4f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Biomimetic Materials - chemical synthesis</topic><topic>Biomimetic Materials - chemistry</topic><topic>Hydrocarbons, Aromatic - chemical synthesis</topic><topic>Hydrocarbons, Aromatic - chemistry</topic><topic>Hydrogen - chemistry</topic><topic>Hydrogenation</topic><topic>Imines - chemical synthesis</topic><topic>Imines - chemistry</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>NADP - chemistry</topic><topic>Phenanthridines - chemical synthesis</topic><topic>Phenanthridines - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Qing-An</creatorcontrib><creatorcontrib>Gao, Kai</creatorcontrib><creatorcontrib>Duan, Ying</creatorcontrib><creatorcontrib>Ye, Zhi-Shi</creatorcontrib><creatorcontrib>Shi, Lei</creatorcontrib><creatorcontrib>Yang, Yan</creatorcontrib><creatorcontrib>Zhou, Yong-Gui</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Qing-An</au><au>Gao, Kai</au><au>Duan, Ying</au><au>Ye, Zhi-Shi</au><au>Shi, Lei</au><au>Yang, Yan</au><au>Zhou, Yong-Gui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2012-02-01</date><risdate>2012</risdate><volume>134</volume><issue>4</issue><spage>2442</spage><epage>2448</epage><pages>2442-2448</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the regeneration of the DHPD under the mild condition. Therefore, the substrate scope is not limited in benzoxazinones; the biomimetic asymmetric hydrogenation of benzoxazines, quinoxalines, and quinolines also gives excellent activities and enantioselectivities. Meanwhile, an unexpected reversal of enantioselectivity was observed between the reactions promoted by the different NAD(P)H models, which is ascribed to the different hydride transfer pathway.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>22239152</pmid><doi>10.1021/ja211684v</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2012-02, Vol.134 (4), p.2442-2448 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_919950345 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Biomimetic Materials - chemical synthesis Biomimetic Materials - chemistry Hydrocarbons, Aromatic - chemical synthesis Hydrocarbons, Aromatic - chemistry Hydrogen - chemistry Hydrogenation Imines - chemical synthesis Imines - chemistry Models, Molecular Molecular Structure NADP - chemistry Phenanthridines - chemical synthesis Phenanthridines - chemistry Stereoisomerism |
| title | Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T09%3A12%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Dihydrophenanthridine:%20A%20New%20and%20Easily%20Regenerable%20NAD(P)H%20Model%20for%20Biomimetic%20Asymmetric%20Hydrogenation&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Chen,%20Qing-An&rft.date=2012-02-01&rft.volume=134&rft.issue=4&rft.spage=2442&rft.epage=2448&rft.pages=2442-2448&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/ja211684v&rft_dat=%3Cproquest_cross%3E919950345%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=919950345&rft_id=info:pmid/22239152&rfr_iscdi=true |