Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media

Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media

Arylboronate esters bearing a pendant Michael-acceptor alkene can add to norbornene and cyclize to give indane systems in yields ranging from 62% to 95% with high diastereomeric excess (>20:1). The reaction is performed in an organic/aqueous emulsion and catalyzed using [Rh(COD)Cl]2 with t-Bu-amp...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2002-06, Vol.4 (12), p.2105-2108
Hauptverfasser: Lautens, Mark, Mancuso, John
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 2108
container_issue 12
container_start_page 2105
container_title Organic letters
container_volume 4
creator Lautens, Mark
Mancuso, John
description Arylboronate esters bearing a pendant Michael-acceptor alkene can add to norbornene and cyclize to give indane systems in yields ranging from 62% to 95% with high diastereomeric excess (>20:1). The reaction is performed in an organic/aqueous emulsion and catalyzed using [Rh(COD)Cl]2 with t-Bu-amphos chloride, a sterically bulky, electron-rich, water-soluble phosphine ligand.
doi_str_mv 10.1021/ol0260627
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71786767</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71786767</sourcerecordid><originalsourceid>FETCH-LOGICAL-a377t-c55a6efcf0e40ec4283aa3ba51deea649f6f713f9bc63b8769e50f6d5d0f50c93</originalsourceid><addsrcrecordid>eNptkEFLAzEQhYMotlYP_gHJRbGHarK7SbrHUlstVATR85JNJpiyu6nJrrD-elNa9OJphuGbN_MeQpeU3FGS0HtXkYQTnogjNKQsSSeCsOT4t-dkgM5C2BBC4yQ_RQOakCyP7RDZBytDCx5cgApUa78AL52vZWtdg53Bq0bLBgI23tV45vuqdN41sgW82O0FPJetrPpv0Ljs8euH07arb1djbBs8--zAdQE_g7byHJ0YWQW4ONQRel8u3uZPk_XL42o-W09kKkQ7UYxJDkYZAhkBlSXTVMq0lIxqAMmz3HAjaGryUvG0nAqeAyOGa6aJYUTl6Qjd7HW33sX7oS1qGxRUVbQRnykEFVMuuIjgeA8q70LwYIqtt7X0fUFJscu1-M01slcH0a6sQf-RhyAjcL0HpArFxnW-iR7_EfoBKI5_2Q</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71786767</pqid></control><display><type>article</type><title>Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media</title><source>ACS Publications</source><creator>Lautens, Mark ; Mancuso, John</creator><creatorcontrib>Lautens, Mark ; Mancuso, John</creatorcontrib><description>Arylboronate esters bearing a pendant Michael-acceptor alkene can add to norbornene and cyclize to give indane systems in yields ranging from 62% to 95% with high diastereomeric excess (&gt;20:1). The reaction is performed in an organic/aqueous emulsion and catalyzed using [Rh(COD)Cl]2 with t-Bu-amphos chloride, a sterically bulky, electron-rich, water-soluble phosphine ligand.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0260627</identifier><identifier>PMID: 12049529</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2002-06, Vol.4 (12), p.2105-2108</ispartof><rights>Copyright © 2002 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-c55a6efcf0e40ec4283aa3ba51deea649f6f713f9bc63b8769e50f6d5d0f50c93</citedby><cites>FETCH-LOGICAL-a377t-c55a6efcf0e40ec4283aa3ba51deea649f6f713f9bc63b8769e50f6d5d0f50c93</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/ol0260627$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol0260627$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12049529$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lautens, Mark</creatorcontrib><creatorcontrib>Mancuso, John</creatorcontrib><title>Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Arylboronate esters bearing a pendant Michael-acceptor alkene can add to norbornene and cyclize to give indane systems in yields ranging from 62% to 95% with high diastereomeric excess (&gt;20:1). The reaction is performed in an organic/aqueous emulsion and catalyzed using [Rh(COD)Cl]2 with t-Bu-amphos chloride, a sterically bulky, electron-rich, water-soluble phosphine ligand.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNptkEFLAzEQhYMotlYP_gHJRbGHarK7SbrHUlstVATR85JNJpiyu6nJrrD-elNa9OJphuGbN_MeQpeU3FGS0HtXkYQTnogjNKQsSSeCsOT4t-dkgM5C2BBC4yQ_RQOakCyP7RDZBytDCx5cgApUa78AL52vZWtdg53Bq0bLBgI23tV45vuqdN41sgW82O0FPJetrPpv0Ljs8euH07arb1djbBs8--zAdQE_g7byHJ0YWQW4ONQRel8u3uZPk_XL42o-W09kKkQ7UYxJDkYZAhkBlSXTVMq0lIxqAMmz3HAjaGryUvG0nAqeAyOGa6aJYUTl6Qjd7HW33sX7oS1qGxRUVbQRnykEFVMuuIjgeA8q70LwYIqtt7X0fUFJscu1-M01slcH0a6sQf-RhyAjcL0HpArFxnW-iR7_EfoBKI5_2Q</recordid><startdate>20020613</startdate><enddate>20020613</enddate><creator>Lautens, Mark</creator><creator>Mancuso, John</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20020613</creationdate><title>Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media</title><author>Lautens, Mark ; Mancuso, John</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-c55a6efcf0e40ec4283aa3ba51deea649f6f713f9bc63b8769e50f6d5d0f50c93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lautens, Mark</creatorcontrib><creatorcontrib>Mancuso, John</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lautens, Mark</au><au>Mancuso, John</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2002-06-13</date><risdate>2002</risdate><volume>4</volume><issue>12</issue><spage>2105</spage><epage>2108</epage><pages>2105-2108</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Arylboronate esters bearing a pendant Michael-acceptor alkene can add to norbornene and cyclize to give indane systems in yields ranging from 62% to 95% with high diastereomeric excess (&gt;20:1). The reaction is performed in an organic/aqueous emulsion and catalyzed using [Rh(COD)Cl]2 with t-Bu-amphos chloride, a sterically bulky, electron-rich, water-soluble phosphine ligand.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>12049529</pmid><doi>10.1021/ol0260627</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2002-06, Vol.4 (12), p.2105-2108
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_71786767
source ACS Publications
title Diastereoselective Formation of Indanes from Arylboronate Esters Catalyzed by Rhodium(I) in Aqueous Media
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-05T14%3A51%3A28IST&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=Diastereoselective%20Formation%20of%20Indanes%20from%20Arylboronate%20Esters%20Catalyzed%20by%20Rhodium(I)%20in%20Aqueous%20Media&rft.jtitle=Organic%20letters&rft.au=Lautens,%20Mark&rft.date=2002-06-13&rft.volume=4&rft.issue=12&rft.spage=2105&rft.epage=2108&rft.pages=2105-2108&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol0260627&rft_dat=%3Cproquest_cross%3E71786767%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=71786767&rft_id=info:pmid/12049529&rfr_iscdi=true