Synthesis and Chemistry of Bridgehead Allylsilanes. Stereoselective Reactions with Aldehydes

A type II intramolecular Diels−Alder reaction provides access to bicyclo[5.3.1] ring systems with an imbedded bridgehead allylsilane. The Lewis acid catalyzed reactions of these compounds with aldehydes proceed efficiently and with control of stereochemistry.

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2005-09, Vol.7 (18), p.3913-3916
Hauptverfasser: Lauchli, Ryan, Whitney, John M, Zhu, Liang, Shea, Kenneth J
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3916
container_issue 18
container_start_page 3913
container_title Organic letters
container_volume 7
creator Lauchli, Ryan
Whitney, John M
Zhu, Liang
Shea, Kenneth J
description A type II intramolecular Diels−Alder reaction provides access to bicyclo[5.3.1] ring systems with an imbedded bridgehead allylsilane. The Lewis acid catalyzed reactions of these compounds with aldehydes proceed efficiently and with control of stereochemistry.
doi_str_mv 10.1021/ol051363c
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68518242</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68518242</sourcerecordid><originalsourceid>FETCH-LOGICAL-a313t-8e98c475d554a53777a0749d54cbd271df7c6c63b2852eaa2d8a0a86048e9a633</originalsourceid><addsrcrecordid>eNptkEtLAzEUhYMotlYX_gHJRsFFNY9JZmZZiy8oCFZ3wpAmd5wp6aQmM8r8e1Na6sbVPVy-e7jnIHROyQ0ljN46SwTlkusDNKSC8XFKBDvca0kG6CSEJSE0bvJjNKCS0jznZIg-5n3TVhDqgFVj8LSCVR1a32NX4jtfm0-oQBk8sba3obaqgXCD5y14cAEs6Lb-BvwKKgrXBPxTt1WEDVS9gXCKjkplA5zt5gi9P9y_TZ_Gs5fH5-lkNlac8nacQZ7pJBVGiEQJnqapImmSG5HohWEpNWWqpZZ8wTLBQClmMkVUJkkSL5XkfISutr5r7746CG0RQ2iwm3ddFwqZCZqxhEXwegtq70LwUBZrX6-U7wtKik2Vxb7KyF7sTLvFCswfuesuApdbQOlQLF3nm5jxH6NfsJZ6-A</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68518242</pqid></control><display><type>article</type><title>Synthesis and Chemistry of Bridgehead Allylsilanes. Stereoselective Reactions with Aldehydes</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Lauchli, Ryan ; Whitney, John M ; Zhu, Liang ; Shea, Kenneth J</creator><creatorcontrib>Lauchli, Ryan ; Whitney, John M ; Zhu, Liang ; Shea, Kenneth J</creatorcontrib><description>A type II intramolecular Diels−Alder reaction provides access to bicyclo[5.3.1] ring systems with an imbedded bridgehead allylsilane. The Lewis acid catalyzed reactions of these compounds with aldehydes proceed efficiently and with control of stereochemistry.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol051363c</identifier><identifier>PMID: 16119930</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Aldehydes - chemistry ; Catalysis ; Molecular Structure ; Silanes - chemical synthesis ; Silanes - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2005-09, Vol.7 (18), p.3913-3916</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a313t-8e98c475d554a53777a0749d54cbd271df7c6c63b2852eaa2d8a0a86048e9a633</citedby><cites>FETCH-LOGICAL-a313t-8e98c475d554a53777a0749d54cbd271df7c6c63b2852eaa2d8a0a86048e9a633</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/ol051363c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol051363c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27059,27907,27908,56721,56771</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16119930$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lauchli, Ryan</creatorcontrib><creatorcontrib>Whitney, John M</creatorcontrib><creatorcontrib>Zhu, Liang</creatorcontrib><creatorcontrib>Shea, Kenneth J</creatorcontrib><title>Synthesis and Chemistry of Bridgehead Allylsilanes. Stereoselective Reactions with Aldehydes</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A type II intramolecular Diels−Alder reaction provides access to bicyclo[5.3.1] ring systems with an imbedded bridgehead allylsilane. The Lewis acid catalyzed reactions of these compounds with aldehydes proceed efficiently and with control of stereochemistry.</description><subject>Aldehydes - chemistry</subject><subject>Catalysis</subject><subject>Molecular Structure</subject><subject>Silanes - chemical synthesis</subject><subject>Silanes - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtLAzEUhYMotlYX_gHJRsFFNY9JZmZZiy8oCFZ3wpAmd5wp6aQmM8r8e1Na6sbVPVy-e7jnIHROyQ0ljN46SwTlkusDNKSC8XFKBDvca0kG6CSEJSE0bvJjNKCS0jznZIg-5n3TVhDqgFVj8LSCVR1a32NX4jtfm0-oQBk8sba3obaqgXCD5y14cAEs6Lb-BvwKKgrXBPxTt1WEDVS9gXCKjkplA5zt5gi9P9y_TZ_Gs5fH5-lkNlac8nacQZ7pJBVGiEQJnqapImmSG5HohWEpNWWqpZZ8wTLBQClmMkVUJkkSL5XkfISutr5r7746CG0RQ2iwm3ddFwqZCZqxhEXwegtq70LwUBZrX6-U7wtKik2Vxb7KyF7sTLvFCswfuesuApdbQOlQLF3nm5jxH6NfsJZ6-A</recordid><startdate>20050901</startdate><enddate>20050901</enddate><creator>Lauchli, Ryan</creator><creator>Whitney, John M</creator><creator>Zhu, Liang</creator><creator>Shea, Kenneth J</creator><general>American Chemical Society</general><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>20050901</creationdate><title>Synthesis and Chemistry of Bridgehead Allylsilanes. Stereoselective Reactions with Aldehydes</title><author>Lauchli, Ryan ; Whitney, John M ; Zhu, Liang ; Shea, Kenneth J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-8e98c475d554a53777a0749d54cbd271df7c6c63b2852eaa2d8a0a86048e9a633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Aldehydes - chemistry</topic><topic>Catalysis</topic><topic>Molecular Structure</topic><topic>Silanes - chemical synthesis</topic><topic>Silanes - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lauchli, Ryan</creatorcontrib><creatorcontrib>Whitney, John M</creatorcontrib><creatorcontrib>Zhu, Liang</creatorcontrib><creatorcontrib>Shea, Kenneth J</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lauchli, Ryan</au><au>Whitney, John M</au><au>Zhu, Liang</au><au>Shea, Kenneth J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Chemistry of Bridgehead Allylsilanes. Stereoselective Reactions with Aldehydes</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2005-09-01</date><risdate>2005</risdate><volume>7</volume><issue>18</issue><spage>3913</spage><epage>3916</epage><pages>3913-3916</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A type II intramolecular Diels−Alder reaction provides access to bicyclo[5.3.1] ring systems with an imbedded bridgehead allylsilane. The Lewis acid catalyzed reactions of these compounds with aldehydes proceed efficiently and with control of stereochemistry.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>16119930</pmid><doi>10.1021/ol051363c</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2005-09, Vol.7 (18), p.3913-3916
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_68518242
source MEDLINE; American Chemical Society Journals
subjects Aldehydes - chemistry
Catalysis
Molecular Structure
Silanes - chemical synthesis
Silanes - chemistry
Stereoisomerism
title Synthesis and Chemistry of Bridgehead Allylsilanes. Stereoselective Reactions with Aldehydes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-16T10%3A15%3A48IST&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=Synthesis%20and%20Chemistry%20of%20Bridgehead%20Allylsilanes.%20Stereoselective%20Reactions%20with%20Aldehydes&rft.jtitle=Organic%20letters&rft.au=Lauchli,%20Ryan&rft.date=2005-09-01&rft.volume=7&rft.issue=18&rft.spage=3913&rft.epage=3916&rft.pages=3913-3916&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol051363c&rft_dat=%3Cproquest_cross%3E68518242%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=68518242&rft_id=info:pmid/16119930&rfr_iscdi=true