New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements

Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including α-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of the American Chemical Society 2006-04, Vol.128 (14), p.4568-4569
Hauptverfasser:	Chen, Yi-Hung, McDonald, Frank E
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetates - chemistry Aldehydes - chemistry Chemistry Diphosphonates - chemistry Exact sciences and technology Hydrogen Peroxide - chemistry Organic chemistry Propionates - chemical synthesis Propionates - chemistry Pyrones - chemical synthesis Pyrones - chemistry Stereoisomerism
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	4569
container_issue	14
container_start_page	4568
container_title	Journal of the American Chemical Society
container_volume	128
creator	Chen, Yi-Hung McDonald, Frank E
description	Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including α-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.
doi_str_mv	10.1021/ja061082f
format	Article
fullrecord	<record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_ja061082f</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c101486137</sourcerecordid><originalsourceid>FETCH-LOGICAL-a482t-69b704d1cacb376b2ca891da0f1d8f82667398776f37bb0f8ff1cd15ebbaccd73</originalsourceid><addsrcrecordid>eNptkMFOGzEURa0K1KShi_5A5Q0LFgO2J2N7ljAiJVIEiFB1ab3x2I1DMh7ZE0r-oOt-Il9So0Rkw-rp6p13dd9F6Bsl55QwerEEwimRzH5CQ1owkhWU8SM0JISwTEieD9CXGJdJjpmkn9GA8qIcc8mGqLs1f3C1cAFWeL5t-4VvI7Y-4GtrnXam7fG07YNvNrp3vsXe4isXu-C7pKA3ET87wPPeBONjZ7RLV_juxbcOXv_-q3xn8IOBEKD9bdbJLZ6gYwuraL7u5wj9nFw_VjfZ7O7HtLqcZTCWrM94WQsybqgGXeeC10yDLGkDxNJGWsk4F3kpheA2F3VNrLSW6oYWpq5B60bkI3S289XBxxiMVV1wawhbRYl6a029t5bY7zu229Rr0xzIfU0JON0DEDWsbHpHu3jghCA5KXnish3nYm9e3vcQnlTKKwr1eD9XN5PyF5ldVUocfEFHtfSb0KZKPgj4H_1Zkz4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements</title><source>MEDLINE</source><source>ACS Journals: American Chemical Society Web Editions</source><creator>Chen, Yi-Hung ; McDonald, Frank E</creator><creatorcontrib>Chen, Yi-Hung ; McDonald, Frank E</creatorcontrib><description>Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including α-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja061082f</identifier><identifier>PMID: 16594682</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acetates - chemistry ; Aldehydes - chemistry ; Chemistry ; Diphosphonates - chemistry ; Exact sciences and technology ; Hydrogen Peroxide - chemistry ; Organic chemistry ; Propionates - chemical synthesis ; Propionates - chemistry ; Pyrones - chemical synthesis ; Pyrones - chemistry ; Stereoisomerism</subject><ispartof>Journal of the American Chemical Society, 2006-04, Vol.128 (14), p.4568-4569</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a482t-69b704d1cacb376b2ca891da0f1d8f82667398776f37bb0f8ff1cd15ebbaccd73</citedby><cites>FETCH-LOGICAL-a482t-69b704d1cacb376b2ca891da0f1d8f82667398776f37bb0f8ff1cd15ebbaccd73</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/ja061082f$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja061082f$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2756,27067,27915,27916,56729,56779</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17703096$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16594682$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Yi-Hung</creatorcontrib><creatorcontrib>McDonald, Frank E</creatorcontrib><title>New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including α-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.</description><subject>Acetates - chemistry</subject><subject>Aldehydes - chemistry</subject><subject>Chemistry</subject><subject>Diphosphonates - chemistry</subject><subject>Exact sciences and technology</subject><subject>Hydrogen Peroxide - chemistry</subject><subject>Organic chemistry</subject><subject>Propionates - chemical synthesis</subject><subject>Propionates - chemistry</subject><subject>Pyrones - chemical synthesis</subject><subject>Pyrones - chemistry</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMFOGzEURa0K1KShi_5A5Q0LFgO2J2N7ljAiJVIEiFB1ab3x2I1DMh7ZE0r-oOt-Il9So0Rkw-rp6p13dd9F6Bsl55QwerEEwimRzH5CQ1owkhWU8SM0JISwTEieD9CXGJdJjpmkn9GA8qIcc8mGqLs1f3C1cAFWeL5t-4VvI7Y-4GtrnXam7fG07YNvNrp3vsXe4isXu-C7pKA3ET87wPPeBONjZ7RLV_juxbcOXv_-q3xn8IOBEKD9bdbJLZ6gYwuraL7u5wj9nFw_VjfZ7O7HtLqcZTCWrM94WQsybqgGXeeC10yDLGkDxNJGWsk4F3kpheA2F3VNrLSW6oYWpq5B60bkI3S289XBxxiMVV1wawhbRYl6a029t5bY7zu229Rr0xzIfU0JON0DEDWsbHpHu3jghCA5KXnish3nYm9e3vcQnlTKKwr1eD9XN5PyF5ldVUocfEFHtfSb0KZKPgj4H_1Zkz4</recordid><startdate>20060412</startdate><enddate>20060412</enddate><creator>Chen, Yi-Hung</creator><creator>McDonald, Frank E</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></search><sort><creationdate>20060412</creationdate><title>New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements</title><author>Chen, Yi-Hung ; McDonald, Frank E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a482t-69b704d1cacb376b2ca891da0f1d8f82667398776f37bb0f8ff1cd15ebbaccd73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Acetates - chemistry</topic><topic>Aldehydes - chemistry</topic><topic>Chemistry</topic><topic>Diphosphonates - chemistry</topic><topic>Exact sciences and technology</topic><topic>Hydrogen Peroxide - chemistry</topic><topic>Organic chemistry</topic><topic>Propionates - chemical synthesis</topic><topic>Propionates - chemistry</topic><topic>Pyrones - chemical synthesis</topic><topic>Pyrones - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Yi-Hung</creatorcontrib><creatorcontrib>McDonald, Frank E</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><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Yi-Hung</au><au>McDonald, Frank E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2006-04-12</date><risdate>2006</risdate><volume>128</volume><issue>14</issue><spage>4568</spage><epage>4569</epage><pages>4568-4569</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including α-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16594682</pmid><doi>10.1021/ja061082f</doi><tpages>2</tpages><oa>free_for_read</oa></addata></record>
fulltext	fulltext
identifier	ISSN: 0002-7863
ispartof	Journal of the American Chemical Society, 2006-04, Vol.128 (14), p.4568-4569
issn	0002-7863 1520-5126
language	eng
recordid	cdi_crossref_primary_10_1021_ja061082f
source	MEDLINE; ACS Journals: American Chemical Society Web Editions
subjects	Acetates - chemistry Aldehydes - chemistry Chemistry Diphosphonates - chemistry Exact sciences and technology Hydrogen Peroxide - chemistry Organic chemistry Propionates - chemical synthesis Propionates - chemistry Pyrones - chemical synthesis Pyrones - chemistry Stereoisomerism
title	New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-14T17%3A35%3A14IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=New%20Chiral%20Synthons%20for%20Efficient%20Introduction%20of%20Bispropionates%20via%20Stereospecific%20Oxonia%E2%88%92Cope%20Rearrangements&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Chen,%20Yi-Hung&rft.date=2006-04-12&rft.volume=128&rft.issue=14&rft.spage=4568&rft.epage=4569&rft.pages=4568-4569&rft.issn=0002-7863&rft.eissn=1520-5126&rft.coden=JACSAT&rft_id=info:doi/10.1021/ja061082f&rft_dat=%3Cacs_cross%3Ec101486137%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/16594682&rfr_iscdi=true