Enantioresolution of 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl Oxide Using Inclusion Complex with Chiral 2,2′-Dihydroxy-1,1′-binaphtyl
An enantioresolution of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl oxide (BINAPO) into its enantiomers was achieved using the inclusion complex with a commercially available chiral 2,2′-dihydroxy-1,1′-binaphthyl ((R)-BINOL), giving the two enantiomers with 99% ee and 72% ee, respectively.
Gespeichert in:
Veröffentlicht in: | Journal of organic chemistry 2012-04, Vol.77 (7), p.3595-3597 |
---|---|
Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 3597 |
---|---|
container_issue | 7 |
container_start_page | 3595 |
container_title | Journal of organic chemistry |
container_volume | 77 |
creator | Hatano, Bunpei Hashimoto, Kazuyuki Katagiri, Hiroshi Kijima, Tatsuro Murakami, Satoshi Matsuba, Shigeru Kusakari, Miho |
description | An enantioresolution of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl oxide (BINAPO) into its enantiomers was achieved using the inclusion complex with a commercially available chiral 2,2′-dihydroxy-1,1′-binaphthyl ((R)-BINOL), giving the two enantiomers with 99% ee and 72% ee, respectively. |
doi_str_mv | 10.1021/jo202630p |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_992830193</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>992830193</sourcerecordid><originalsourceid>FETCH-LOGICAL-a344t-ccf77297a3b42321c8e72efff35dfcdc96830fbcd9a7b2e4ba21c92d9d9c14c33</originalsourceid><addsrcrecordid>eNptkMtO3DAUhq2qqAyURV-gyqYqSKTYx8lkvCzDVUKaTVlHji-NkcdO7URMdjwCz8Ij8SR4xAxIqGdzjvR_-o70I_SN4F8EAzm584BhSnH3CU1ICTifMlx8RhOMAXKakl20F-MdTlOW5Re0C0BZRQmeoMdzx11vfFDR2yEdLvM6g2N4fnjKT008lKZrlRtt1_rYtcb5o5wck3XaGMe7tm9Hmy1WRqrsNhr3N7t2wg5xLZr7ZWfVKrs3fZvNWxO43ZrPTDvK4FfjB9lov6IdzW1UB5u9j24vzv_Mr_KbxeX1_PdNzmlR9LkQuqqAVZw2BVAgYqYqUFprWkotpGDTGcW6EZLxqgFVNDwxDCSTTJBCULqPfr56u-D_DSr29dJEoazlTvkh1oxBMhC2Jo9eSRF8jEHpugtmycNYE1yv-6_f-k_s9411aJZKvpHbwhPwYwPwKLjVgTth4jtXVtVsSsp3jouY_ENwqYz_PHwB9qSegg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>992830193</pqid></control><display><type>article</type><title>Enantioresolution of 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl Oxide Using Inclusion Complex with Chiral 2,2′-Dihydroxy-1,1′-binaphtyl</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Hatano, Bunpei ; Hashimoto, Kazuyuki ; Katagiri, Hiroshi ; Kijima, Tatsuro ; Murakami, Satoshi ; Matsuba, Shigeru ; Kusakari, Miho</creator><creatorcontrib>Hatano, Bunpei ; Hashimoto, Kazuyuki ; Katagiri, Hiroshi ; Kijima, Tatsuro ; Murakami, Satoshi ; Matsuba, Shigeru ; Kusakari, Miho</creatorcontrib><description>An enantioresolution of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl oxide (BINAPO) into its enantiomers was achieved using the inclusion complex with a commercially available chiral 2,2′-dihydroxy-1,1′-binaphthyl ((R)-BINOL), giving the two enantiomers with 99% ee and 72% ee, respectively.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo202630p</identifier><identifier>PMID: 22397310</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Catalysis ; Chemistry ; Condensed benzenic and aromatic compounds ; Exact sciences and technology ; Molecular Structure ; Naphthalenes - chemical synthesis ; Naphthalenes - chemistry ; Noncondensed benzenic compounds ; Organic chemistry ; Organometalloidal and organometallic compounds ; P derivatives ; Phosphines - chemical synthesis ; Phosphines - chemistry ; Preparations and properties ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2012-04, Vol.77 (7), p.3595-3597</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a344t-ccf77297a3b42321c8e72efff35dfcdc96830fbcd9a7b2e4ba21c92d9d9c14c33</citedby><cites>FETCH-LOGICAL-a344t-ccf77297a3b42321c8e72efff35dfcdc96830fbcd9a7b2e4ba21c92d9d9c14c33</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/jo202630p$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo202630p$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25778615$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22397310$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hatano, Bunpei</creatorcontrib><creatorcontrib>Hashimoto, Kazuyuki</creatorcontrib><creatorcontrib>Katagiri, Hiroshi</creatorcontrib><creatorcontrib>Kijima, Tatsuro</creatorcontrib><creatorcontrib>Murakami, Satoshi</creatorcontrib><creatorcontrib>Matsuba, Shigeru</creatorcontrib><creatorcontrib>Kusakari, Miho</creatorcontrib><title>Enantioresolution of 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl Oxide Using Inclusion Complex with Chiral 2,2′-Dihydroxy-1,1′-binaphtyl</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An enantioresolution of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl oxide (BINAPO) into its enantiomers was achieved using the inclusion complex with a commercially available chiral 2,2′-dihydroxy-1,1′-binaphthyl ((R)-BINOL), giving the two enantiomers with 99% ee and 72% ee, respectively.</description><subject>Catalysis</subject><subject>Chemistry</subject><subject>Condensed benzenic and aromatic compounds</subject><subject>Exact sciences and technology</subject><subject>Molecular Structure</subject><subject>Naphthalenes - chemical synthesis</subject><subject>Naphthalenes - chemistry</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>P derivatives</subject><subject>Phosphines - chemical synthesis</subject><subject>Phosphines - chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtO3DAUhq2qqAyURV-gyqYqSKTYx8lkvCzDVUKaTVlHji-NkcdO7URMdjwCz8Ij8SR4xAxIqGdzjvR_-o70I_SN4F8EAzm584BhSnH3CU1ICTifMlx8RhOMAXKakl20F-MdTlOW5Re0C0BZRQmeoMdzx11vfFDR2yEdLvM6g2N4fnjKT008lKZrlRtt1_rYtcb5o5wck3XaGMe7tm9Hmy1WRqrsNhr3N7t2wg5xLZr7ZWfVKrs3fZvNWxO43ZrPTDvK4FfjB9lov6IdzW1UB5u9j24vzv_Mr_KbxeX1_PdNzmlR9LkQuqqAVZw2BVAgYqYqUFprWkotpGDTGcW6EZLxqgFVNDwxDCSTTJBCULqPfr56u-D_DSr29dJEoazlTvkh1oxBMhC2Jo9eSRF8jEHpugtmycNYE1yv-6_f-k_s9411aJZKvpHbwhPwYwPwKLjVgTth4jtXVtVsSsp3jouY_ENwqYz_PHwB9qSegg</recordid><startdate>20120406</startdate><enddate>20120406</enddate><creator>Hatano, Bunpei</creator><creator>Hashimoto, Kazuyuki</creator><creator>Katagiri, Hiroshi</creator><creator>Kijima, Tatsuro</creator><creator>Murakami, Satoshi</creator><creator>Matsuba, Shigeru</creator><creator>Kusakari, Miho</creator><general>American Chemical Society</general><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>20120406</creationdate><title>Enantioresolution of 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl Oxide Using Inclusion Complex with Chiral 2,2′-Dihydroxy-1,1′-binaphtyl</title><author>Hatano, Bunpei ; Hashimoto, Kazuyuki ; Katagiri, Hiroshi ; Kijima, Tatsuro ; Murakami, Satoshi ; Matsuba, Shigeru ; Kusakari, Miho</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-ccf77297a3b42321c8e72efff35dfcdc96830fbcd9a7b2e4ba21c92d9d9c14c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Catalysis</topic><topic>Chemistry</topic><topic>Condensed benzenic and aromatic compounds</topic><topic>Exact sciences and technology</topic><topic>Molecular Structure</topic><topic>Naphthalenes - chemical synthesis</topic><topic>Naphthalenes - chemistry</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Organometalloidal and organometallic compounds</topic><topic>P derivatives</topic><topic>Phosphines - chemical synthesis</topic><topic>Phosphines - chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hatano, Bunpei</creatorcontrib><creatorcontrib>Hashimoto, Kazuyuki</creatorcontrib><creatorcontrib>Katagiri, Hiroshi</creatorcontrib><creatorcontrib>Kijima, Tatsuro</creatorcontrib><creatorcontrib>Murakami, Satoshi</creatorcontrib><creatorcontrib>Matsuba, Shigeru</creatorcontrib><creatorcontrib>Kusakari, Miho</creatorcontrib><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 organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hatano, Bunpei</au><au>Hashimoto, Kazuyuki</au><au>Katagiri, Hiroshi</au><au>Kijima, Tatsuro</au><au>Murakami, Satoshi</au><au>Matsuba, Shigeru</au><au>Kusakari, Miho</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioresolution of 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl Oxide Using Inclusion Complex with Chiral 2,2′-Dihydroxy-1,1′-binaphtyl</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-04-06</date><risdate>2012</risdate><volume>77</volume><issue>7</issue><spage>3595</spage><epage>3597</epage><pages>3595-3597</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>An enantioresolution of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl oxide (BINAPO) into its enantiomers was achieved using the inclusion complex with a commercially available chiral 2,2′-dihydroxy-1,1′-binaphthyl ((R)-BINOL), giving the two enantiomers with 99% ee and 72% ee, respectively.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22397310</pmid><doi>10.1021/jo202630p</doi><tpages>3</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0022-3263 |
ispartof | Journal of organic chemistry, 2012-04, Vol.77 (7), p.3595-3597 |
issn | 0022-3263 1520-6904 |
language | eng |
recordid | cdi_proquest_miscellaneous_992830193 |
source | MEDLINE; American Chemical Society Journals |
subjects | Catalysis Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Molecular Structure Naphthalenes - chemical synthesis Naphthalenes - chemistry Noncondensed benzenic compounds Organic chemistry Organometalloidal and organometallic compounds P derivatives Phosphines - chemical synthesis Phosphines - chemistry Preparations and properties Stereoisomerism |
title | Enantioresolution of 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl Oxide Using Inclusion Complex with Chiral 2,2′-Dihydroxy-1,1′-binaphtyl |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-04T21%3A04%3A59IST&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=Enantioresolution%20of%202,2%E2%80%B2-Bis(diphenylphosphino)-1,1%E2%80%B2-binaphthyl%20Oxide%20Using%20Inclusion%20Complex%20with%20Chiral%202,2%E2%80%B2-Dihydroxy-1,1%E2%80%B2-binaphtyl&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Hatano,%20Bunpei&rft.date=2012-04-06&rft.volume=77&rft.issue=7&rft.spage=3595&rft.epage=3597&rft.pages=3595-3597&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo202630p&rft_dat=%3Cproquest_cross%3E992830193%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=992830193&rft_id=info:pmid/22397310&rfr_iscdi=true |