Functionalization of Silyldienol Ethers at the γ‑Position via 2‑Silyloxypentadienyl Cations

This report describes Brønsted acid catalyzed de novo synthesis of silyldienol ethers bearing tetrasubstituted double bonds via an intermediacy of 2-silyloxypentadienyl cations. The reactivity of these novel cationic intermediates could be modulated and harnessed toward direct nucleophilic additions...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2016-03, Vol.18 (5), p.1084-1087
Hauptverfasser:	Ayala, Caitlan E, Dange, Nitin S, Stepherson, Jacob R, Henry, Jeffrey L, Fronczek, Frank R, Kartika, Rendy
Format:	Artikel
Sprache:	eng
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	1087
container_issue	5
container_start_page	1084
container_title	Organic letters
container_volume	18
creator	Ayala, Caitlan E Dange, Nitin S Stepherson, Jacob R Henry, Jeffrey L Fronczek, Frank R Kartika, Rendy
description	This report describes Brønsted acid catalyzed de novo synthesis of silyldienol ethers bearing tetrasubstituted double bonds via an intermediacy of 2-silyloxypentadienyl cations. The reactivity of these novel cationic intermediates could be modulated and harnessed toward direct nucleophilic additions regioselectively at the γ-position to produce highly functionalized silyldienol ethers with tunable control of the resulting double bond geometry.
doi_str_mv	10.1021/acs.orglett.6b00196
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1770873011</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1770873011</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-3ded4ac3de3216ab4005cf157d1c934925c4119ea2d7e6d2df336f04ca8afe53</originalsourceid><addsrcrecordid>eNp9kEtOwzAURS0EoqWwAiTkIZO0_uTTDFHVAlIlkOjcuLYDrty4xA4ijNgCa2EfLIKV4LShQ0bv6unc96QDwDlGQ4wIHnHhhrZ6Msr7YbpECOfpAejjhNAoQwk53OcU9cCJc6uAhE1-DHokHacZyuM-eJzVpfDaltzod94GaAv4oE1jpFalNXDqn1XlIPcwBPj99fPxeW-d3qKvmkMSFlvevjUbVXre9hoDJ9tr7hQcFdw4ddbNAVjMpovJTTS_u76dXM0jTuPER1QqGXMRBiU45csYoUQUOMkkFjmNc5KIGONccSIzlUoiC0rTAsWCj3mhEjoAl7uzm8q-1Mp5ttZOKGN4qWztGM4yNM5oMBBQukNFZZ2rVME2lV7zqmEYsdYsC2ZZZ5Z1ZkProntQL9dK7jt_KgMw2gFte2XrKih1_578BfIfjGs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1770873011</pqid></control><display><type>article</type><title>Functionalization of Silyldienol Ethers at the γ‑Position via 2‑Silyloxypentadienyl Cations</title><source>American Chemical Society Journals</source><creator>Ayala, Caitlan E ; Dange, Nitin S ; Stepherson, Jacob R ; Henry, Jeffrey L ; Fronczek, Frank R ; Kartika, Rendy</creator><creatorcontrib>Ayala, Caitlan E ; Dange, Nitin S ; Stepherson, Jacob R ; Henry, Jeffrey L ; Fronczek, Frank R ; Kartika, Rendy</creatorcontrib><description>This report describes Brønsted acid catalyzed de novo synthesis of silyldienol ethers bearing tetrasubstituted double bonds via an intermediacy of 2-silyloxypentadienyl cations. The reactivity of these novel cationic intermediates could be modulated and harnessed toward direct nucleophilic additions regioselectively at the γ-position to produce highly functionalized silyldienol ethers with tunable control of the resulting double bond geometry.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.6b00196</identifier><identifier>PMID: 26867094</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2016-03, Vol.18 (5), p.1084-1087</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-3ded4ac3de3216ab4005cf157d1c934925c4119ea2d7e6d2df336f04ca8afe53</citedby><cites>FETCH-LOGICAL-a345t-3ded4ac3de3216ab4005cf157d1c934925c4119ea2d7e6d2df336f04ca8afe53</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/acs.orglett.6b00196$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.6b00196$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26867094$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ayala, Caitlan E</creatorcontrib><creatorcontrib>Dange, Nitin S</creatorcontrib><creatorcontrib>Stepherson, Jacob R</creatorcontrib><creatorcontrib>Henry, Jeffrey L</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Kartika, Rendy</creatorcontrib><title>Functionalization of Silyldienol Ethers at the γ‑Position via 2‑Silyloxypentadienyl Cations</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>This report describes Brønsted acid catalyzed de novo synthesis of silyldienol ethers bearing tetrasubstituted double bonds via an intermediacy of 2-silyloxypentadienyl cations. The reactivity of these novel cationic intermediates could be modulated and harnessed toward direct nucleophilic additions regioselectively at the γ-position to produce highly functionalized silyldienol ethers with tunable control of the resulting double bond geometry.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9kEtOwzAURS0EoqWwAiTkIZO0_uTTDFHVAlIlkOjcuLYDrty4xA4ijNgCa2EfLIKV4LShQ0bv6unc96QDwDlGQ4wIHnHhhrZ6Msr7YbpECOfpAejjhNAoQwk53OcU9cCJc6uAhE1-DHokHacZyuM-eJzVpfDaltzod94GaAv4oE1jpFalNXDqn1XlIPcwBPj99fPxeW-d3qKvmkMSFlvevjUbVXre9hoDJ9tr7hQcFdw4ddbNAVjMpovJTTS_u76dXM0jTuPER1QqGXMRBiU45csYoUQUOMkkFjmNc5KIGONccSIzlUoiC0rTAsWCj3mhEjoAl7uzm8q-1Mp5ttZOKGN4qWztGM4yNM5oMBBQukNFZZ2rVME2lV7zqmEYsdYsC2ZZZ5Z1ZkProntQL9dK7jt_KgMw2gFte2XrKih1_578BfIfjGs</recordid><startdate>20160304</startdate><enddate>20160304</enddate><creator>Ayala, Caitlan E</creator><creator>Dange, Nitin S</creator><creator>Stepherson, Jacob R</creator><creator>Henry, Jeffrey L</creator><creator>Fronczek, Frank R</creator><creator>Kartika, Rendy</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20160304</creationdate><title>Functionalization of Silyldienol Ethers at the γ‑Position via 2‑Silyloxypentadienyl Cations</title><author>Ayala, Caitlan E ; Dange, Nitin S ; Stepherson, Jacob R ; Henry, Jeffrey L ; Fronczek, Frank R ; Kartika, Rendy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-3ded4ac3de3216ab4005cf157d1c934925c4119ea2d7e6d2df336f04ca8afe53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ayala, Caitlan E</creatorcontrib><creatorcontrib>Dange, Nitin S</creatorcontrib><creatorcontrib>Stepherson, Jacob R</creatorcontrib><creatorcontrib>Henry, Jeffrey L</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Kartika, Rendy</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>Ayala, Caitlan E</au><au>Dange, Nitin S</au><au>Stepherson, Jacob R</au><au>Henry, Jeffrey L</au><au>Fronczek, Frank R</au><au>Kartika, Rendy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Functionalization of Silyldienol Ethers at the γ‑Position via 2‑Silyloxypentadienyl Cations</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2016-03-04</date><risdate>2016</risdate><volume>18</volume><issue>5</issue><spage>1084</spage><epage>1087</epage><pages>1084-1087</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>This report describes Brønsted acid catalyzed de novo synthesis of silyldienol ethers bearing tetrasubstituted double bonds via an intermediacy of 2-silyloxypentadienyl cations. The reactivity of these novel cationic intermediates could be modulated and harnessed toward direct nucleophilic additions regioselectively at the γ-position to produce highly functionalized silyldienol ethers with tunable control of the resulting double bond geometry.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26867094</pmid><doi>10.1021/acs.orglett.6b00196</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 1523-7060
ispartof	Organic letters, 2016-03, Vol.18 (5), p.1084-1087
issn	1523-7060 1523-7052
language	eng
recordid	cdi_proquest_miscellaneous_1770873011
source	American Chemical Society Journals
title	Functionalization of Silyldienol Ethers at the γ‑Position via 2‑Silyloxypentadienyl Cations
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T23%3A15%3A17IST&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=Functionalization%20of%20Silyldienol%20Ethers%20at%20the%20%CE%B3%E2%80%91Position%20via%202%E2%80%91Silyloxypentadienyl%20Cations&rft.jtitle=Organic%20letters&rft.au=Ayala,%20Caitlan%20E&rft.date=2016-03-04&rft.volume=18&rft.issue=5&rft.spage=1084&rft.epage=1087&rft.pages=1084-1087&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.6b00196&rft_dat=%3Cproquest_cross%3E1770873011%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=1770873011&rft_id=info:pmid/26867094&rfr_iscdi=true