Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives
New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels–Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels–Alder reactions provided an endo cycloadduct as a major product with m...
Gespeichert in:
| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2002, Vol.50(3), pp.372-379 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 379 |
|---|---|
| container_issue | 3 |
| container_start_page | 372 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 50 |
| creator | Watanabe, Kazuhiro Hirasawa, Takashi Hiroi, Kunio |
| description | New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels–Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels–Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction. |
| doi_str_mv | 10.1248/cpb.50.372 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71531771</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71531771</sourcerecordid><originalsourceid>FETCH-LOGICAL-c561t-407bdbdcd876205cea55d177d6702623975a2cdea9e120269ab697e7ea031d983</originalsourceid><addsrcrecordid>eNpF0M2O0zAQB3ALgdiycOEBUC4gQKT4o44bLijq8iVVQgL2HE3saeuVk3Q96bLZE2_AgTfkSfCqZXvxHOan_8h_xp4KPhVyNn9rt81U86ky8h6bCDUzuZZS3WcTznmZS1WoE_aI6IJzqblRD9mJEKUQkosJ-73En56yynqXL2CAMN6gyyoa2xaH6G125jHQ319_quAwZt8Q7OD7jrJz8t06W2x8hJB934VVf-0dZku_hs7Ru_8bmb-s4hgoAd-NIYVuxvAqF29U3l_DTR98h9kZRn8Fg79CeswerCAQPjnMU3b-8cOPxed8-fXTl0W1zK0uxJDPuGlc46ybm0JybRG0dsIYVxguC6lKo0Fah1Bi-qcsSmiK0qBB4Eq4cq5O2Yt97jb2lzukoW49WQwBOux3VBuhVcoTCb7eQxt7ooireht9C3GsBa9v669T_bXmdao_4WeH1F3TojvSQ98JPD8AIAthFaGzno5O6cKo8jbo_d5d0ABrvAMQB28D3t3cP-n0cbOBWGOn_gEC_KY7</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71531771</pqid></control><display><type>article</type><title>Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives</title><source>J-STAGE Free</source><source>MEDLINE</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>Watanabe, Kazuhiro ; Hirasawa, Takashi ; Hiroi, Kunio</creator><creatorcontrib>Watanabe, Kazuhiro ; Hirasawa, Takashi ; Hiroi, Kunio</creatorcontrib><description>New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels–Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels–Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.50.372</identifier><identifier>PMID: 11911201</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Acids - chemistry ; Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; asymmetric Diels–Alder reaction ; Catalysis ; Chemistry ; chiral 1,3-oxazoline ; chiral ligand ; chiral sulfoxide ; copper catalyst ; Exact sciences and technology ; Lewis acid ; Organic chemistry ; Oxazoles - chemistry ; Preparations and properties ; Spectrum Analysis ; Stereoisomerism ; Sulfoxides - chemistry</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2002, Vol.50(3), pp.372-379</ispartof><rights>2002 The Pharmaceutical Society of Japan</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c561t-407bdbdcd876205cea55d177d6702623975a2cdea9e120269ab697e7ea031d983</citedby><cites>FETCH-LOGICAL-c561t-407bdbdcd876205cea55d177d6702623975a2cdea9e120269ab697e7ea031d983</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13567392$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11911201$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Watanabe, Kazuhiro</creatorcontrib><creatorcontrib>Hirasawa, Takashi</creatorcontrib><creatorcontrib>Hiroi, Kunio</creatorcontrib><title>Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels–Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels–Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction.</description><subject>Acids - chemistry</subject><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>asymmetric Diels–Alder reaction</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>chiral 1,3-oxazoline</subject><subject>chiral ligand</subject><subject>chiral sulfoxide</subject><subject>copper catalyst</subject><subject>Exact sciences and technology</subject><subject>Lewis acid</subject><subject>Organic chemistry</subject><subject>Oxazoles - chemistry</subject><subject>Preparations and properties</subject><subject>Spectrum Analysis</subject><subject>Stereoisomerism</subject><subject>Sulfoxides - chemistry</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0M2O0zAQB3ALgdiycOEBUC4gQKT4o44bLijq8iVVQgL2HE3saeuVk3Q96bLZE2_AgTfkSfCqZXvxHOan_8h_xp4KPhVyNn9rt81U86ky8h6bCDUzuZZS3WcTznmZS1WoE_aI6IJzqblRD9mJEKUQkosJ-73En56yynqXL2CAMN6gyyoa2xaH6G125jHQ319_quAwZt8Q7OD7jrJz8t06W2x8hJB934VVf-0dZku_hs7Ru_8bmb-s4hgoAd-NIYVuxvAqF29U3l_DTR98h9kZRn8Fg79CeswerCAQPjnMU3b-8cOPxed8-fXTl0W1zK0uxJDPuGlc46ybm0JybRG0dsIYVxguC6lKo0Fah1Bi-qcsSmiK0qBB4Eq4cq5O2Yt97jb2lzukoW49WQwBOux3VBuhVcoTCb7eQxt7ooireht9C3GsBa9v669T_bXmdao_4WeH1F3TojvSQ98JPD8AIAthFaGzno5O6cKo8jbo_d5d0ABrvAMQB28D3t3cP-n0cbOBWGOn_gEC_KY7</recordid><startdate>20020301</startdate><enddate>20020301</enddate><creator>Watanabe, Kazuhiro</creator><creator>Hirasawa, Takashi</creator><creator>Hiroi, Kunio</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</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>20020301</creationdate><title>Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives</title><author>Watanabe, Kazuhiro ; Hirasawa, Takashi ; Hiroi, Kunio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c561t-407bdbdcd876205cea55d177d6702623975a2cdea9e120269ab697e7ea031d983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Acids - chemistry</topic><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>asymmetric Diels–Alder reaction</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>chiral 1,3-oxazoline</topic><topic>chiral ligand</topic><topic>chiral sulfoxide</topic><topic>copper catalyst</topic><topic>Exact sciences and technology</topic><topic>Lewis acid</topic><topic>Organic chemistry</topic><topic>Oxazoles - chemistry</topic><topic>Preparations and properties</topic><topic>Spectrum Analysis</topic><topic>Stereoisomerism</topic><topic>Sulfoxides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Watanabe, Kazuhiro</creatorcontrib><creatorcontrib>Hirasawa, Takashi</creatorcontrib><creatorcontrib>Hiroi, Kunio</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>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Watanabe, Kazuhiro</au><au>Hirasawa, Takashi</au><au>Hiroi, Kunio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2002-03-01</date><risdate>2002</risdate><volume>50</volume><issue>3</issue><spage>372</spage><epage>379</epage><pages>372-379</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels–Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels–Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>11911201</pmid><doi>10.1248/cpb.50.372</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 2002, Vol.50(3), pp.372-379 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71531771 |
| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Acids - chemistry Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids asymmetric Diels–Alder reaction Catalysis Chemistry chiral 1,3-oxazoline chiral ligand chiral sulfoxide copper catalyst Exact sciences and technology Lewis acid Organic chemistry Oxazoles - chemistry Preparations and properties Spectrum Analysis Stereoisomerism Sulfoxides - chemistry |
| title | Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions Using Chiral Sulfoxide Ligands: Chiral 2-(Arylsulfinylmethyl)-1,3-oxazoline Derivatives |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T00%3A14%3A02IST&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=Lewis%20Acid-Catalyzed%20Asymmetric%20Diels%E2%80%93Alder%20Reactions%20Using%20Chiral%20Sulfoxide%20Ligands:%20Chiral%202-(Arylsulfinylmethyl)-1,3-oxazoline%20Derivatives&rft.jtitle=Chemical%20&%20pharmaceutical%20bulletin&rft.au=Watanabe,%20Kazuhiro&rft.date=2002-03-01&rft.volume=50&rft.issue=3&rft.spage=372&rft.epage=379&rft.pages=372-379&rft.issn=0009-2363&rft.eissn=1347-5223&rft.coden=CPBTAL&rft_id=info:doi/10.1248/cpb.50.372&rft_dat=%3Cproquest_cross%3E71531771%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=71531771&rft_id=info:pmid/11911201&rfr_iscdi=true |