Enantioselective Hydrogenation of 3-Alkylidenelactams: High-Throughput Screening Provides a Surprising Solution
High-throughput screening of 256 potential catalysts (8 metal precursors × 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the inef...
Gespeichert in:
| Veröffentlicht in: | Journal of the American Chemical Society 2002-11, Vol.124 (46), p.13692-13693 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 13693 |
|---|---|
| container_issue | 46 |
| container_start_page | 13692 |
| container_title | Journal of the American Chemical Society |
| container_volume | 124 |
| creator | Yue, Tai-Yuen Nugent, William A |
| description | High-throughput screening of 256 potential catalysts (8 metal precursors × 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level. |
| doi_str_mv | 10.1021/ja028043y |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72679454</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72679454</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-a0cdfe451902981c64e9b3a15ba606177d30fa25eddca523c9f3353f1408c7ce3</originalsourceid><addsrcrecordid>eNpt0MtuEzEUBmALgWgoLHgBNBuQWAz4Ohd2VVUIUiWKEgQ768RzJnHq2MGeqciObV-zT4KjRM2GleVzPv06-gl5zegHRjn7uAbKGyrF7gmZMMVpqRivnpIJpZSXdVOJM_IipXX-St6w5-SMcSkYbasJiVce_GBDQodmsHdYTHddDEv0kKe-CH0hygt3u3O2Q48OzACb9Onh730xtctVOV_FMC5X23EoZiYieuuXxU0Md5mnAorZGLfRpv10Fty4z3xJnvXgEr46vufkx-er-eW0vP725evlxXUJom6HEqjpepSKtZS3DTOVxHYhgKkFVLRidd0J2gNX2HUGFBem7YVQomeSNqY2KM7Ju0PuNobfI6ZBb2wy6Bx4DGPSNa_qViqZ4fsDNDGkFLHX-eQNxJ1mVO8L1o8FZ_vmGDouNtid5LHRDN4eASQDro_gjU0nJ6mgSrHsyoOzacA_j3uIt7qqRa30_Gam2fy74r_kT81PuWCSXocx-tzdfw78ByO_oHw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>72679454</pqid></control><display><type>article</type><title>Enantioselective Hydrogenation of 3-Alkylidenelactams: High-Throughput Screening Provides a Surprising Solution</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Yue, Tai-Yuen ; Nugent, William A</creator><creatorcontrib>Yue, Tai-Yuen ; Nugent, William A</creatorcontrib><description>High-throughput screening of 256 potential catalysts (8 metal precursors × 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja028043y</identifier><identifier>PMID: 12431096</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkadienes - chemistry ; Alkenes - chemistry ; Chemical reactivity ; Chemistry ; Exact sciences and technology ; Hydrogenation ; Lactams - chemistry ; Organic chemistry ; Pentanes - chemistry ; Phosphines - chemistry ; Reactivity and mechanisms ; Stereoisomerism</subject><ispartof>Journal of the American Chemical Society, 2002-11, Vol.124 (46), p.13692-13693</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-a0cdfe451902981c64e9b3a15ba606177d30fa25eddca523c9f3353f1408c7ce3</citedby><cites>FETCH-LOGICAL-a379t-a0cdfe451902981c64e9b3a15ba606177d30fa25eddca523c9f3353f1408c7ce3</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/ja028043y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja028043y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14030551$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12431096$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yue, Tai-Yuen</creatorcontrib><creatorcontrib>Nugent, William A</creatorcontrib><title>Enantioselective Hydrogenation of 3-Alkylidenelactams: High-Throughput Screening Provides a Surprising Solution</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>High-throughput screening of 256 potential catalysts (8 metal precursors × 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level.</description><subject>Alkadienes - chemistry</subject><subject>Alkenes - chemistry</subject><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Hydrogenation</subject><subject>Lactams - chemistry</subject><subject>Organic chemistry</subject><subject>Pentanes - chemistry</subject><subject>Phosphines - chemistry</subject><subject>Reactivity and mechanisms</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtuEzEUBmALgWgoLHgBNBuQWAz4Ohd2VVUIUiWKEgQ768RzJnHq2MGeqciObV-zT4KjRM2GleVzPv06-gl5zegHRjn7uAbKGyrF7gmZMMVpqRivnpIJpZSXdVOJM_IipXX-St6w5-SMcSkYbasJiVce_GBDQodmsHdYTHddDEv0kKe-CH0hygt3u3O2Q48OzACb9Onh730xtctVOV_FMC5X23EoZiYieuuXxU0Md5mnAorZGLfRpv10Fty4z3xJnvXgEr46vufkx-er-eW0vP725evlxXUJom6HEqjpepSKtZS3DTOVxHYhgKkFVLRidd0J2gNX2HUGFBem7YVQomeSNqY2KM7Ju0PuNobfI6ZBb2wy6Bx4DGPSNa_qViqZ4fsDNDGkFLHX-eQNxJ1mVO8L1o8FZ_vmGDouNtid5LHRDN4eASQDro_gjU0nJ6mgSrHsyoOzacA_j3uIt7qqRa30_Gam2fy74r_kT81PuWCSXocx-tzdfw78ByO_oHw</recordid><startdate>20021120</startdate><enddate>20021120</enddate><creator>Yue, Tai-Yuen</creator><creator>Nugent, William A</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><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>20021120</creationdate><title>Enantioselective Hydrogenation of 3-Alkylidenelactams: High-Throughput Screening Provides a Surprising Solution</title><author>Yue, Tai-Yuen ; Nugent, William A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-a0cdfe451902981c64e9b3a15ba606177d30fa25eddca523c9f3353f1408c7ce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Alkadienes - chemistry</topic><topic>Alkenes - chemistry</topic><topic>Chemical reactivity</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Hydrogenation</topic><topic>Lactams - chemistry</topic><topic>Organic chemistry</topic><topic>Pentanes - chemistry</topic><topic>Phosphines - chemistry</topic><topic>Reactivity and mechanisms</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yue, Tai-Yuen</creatorcontrib><creatorcontrib>Nugent, William A</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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>Yue, Tai-Yuen</au><au>Nugent, William A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Hydrogenation of 3-Alkylidenelactams: High-Throughput Screening Provides a Surprising Solution</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2002-11-20</date><risdate>2002</risdate><volume>124</volume><issue>46</issue><spage>13692</spage><epage>13693</epage><pages>13692-13693</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>High-throughput screening of 256 potential catalysts (8 metal precursors × 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12431096</pmid><doi>10.1021/ja028043y</doi><tpages>2</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2002-11, Vol.124 (46), p.13692-13693 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_72679454 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkadienes - chemistry Alkenes - chemistry Chemical reactivity Chemistry Exact sciences and technology Hydrogenation Lactams - chemistry Organic chemistry Pentanes - chemistry Phosphines - chemistry Reactivity and mechanisms Stereoisomerism |
| title | Enantioselective Hydrogenation of 3-Alkylidenelactams: High-Throughput Screening Provides a Surprising Solution |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T02%3A12%3A27IST&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=Enantioselective%20Hydrogenation%20of%203-Alkylidenelactams:%E2%80%89%20High-Throughput%20Screening%20Provides%20a%20Surprising%20Solution&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Yue,%20Tai-Yuen&rft.date=2002-11-20&rft.volume=124&rft.issue=46&rft.spage=13692&rft.epage=13693&rft.pages=13692-13693&rft.issn=0002-7863&rft.eissn=1520-5126&rft.coden=JACSAT&rft_id=info:doi/10.1021/ja028043y&rft_dat=%3Cproquest_cross%3E72679454%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=72679454&rft_id=info:pmid/12431096&rfr_iscdi=true |