Bifunctional Molecular Linchpins: A Three-Component Coupling Protocol Employing 2-Bromoallyltrimethylsilane
ABSTRACT A new three-component coupling protocol, exploiting 2-bromoallyltrimethylsilane as a bifunctional linchpin, has been developed. The reaction sequence entails the following steps: lithiation of the vinyl bromide, addition of an aromatic or aliphatic aldehyde, execution of a solvent controlle...
Gespeichert in:
| Veröffentlicht in: | Synlett 2004-07, Vol.2004 (8), p.1363-1366 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1366 |
|---|---|
| container_issue | 8 |
| container_start_page | 1363 |
| container_title | Synlett |
| container_volume | 2004 |
| creator | Smith III, Amos B. Duffey, Matthew O. |
| description | ABSTRACT
A new three-component coupling protocol, exploiting 2-bromoallyltrimethylsilane as a bifunctional linchpin, has been developed. The reaction sequence entails the following steps: lithiation of the vinyl bromide, addition of an aromatic or aliphatic aldehyde, execution of a solvent controlled 1,4-Brook rearrangement induced by HMPA to generate an allyl anion, and addition of a reactive second electrophile. Yields are moderate to good. |
| doi_str_mv | 10.1055/s-2004-825621 |
| format | Article |
| fullrecord | <record><control><sourceid>thieme_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1055_s_2004_825621</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1055_s_2004_825621</sourcerecordid><originalsourceid>FETCH-LOGICAL-c272t-b1eb28f7e60670a840ac660ed56c6cea77f2a4565eca2cee6c538542a97b370e3</originalsourceid><addsrcrecordid>eNp1kL1OwzAYRS0EEqUwsucBMNhObCdsbVR-pCIYyhy55gtxcezIdoa8PanKynSlq6Orq4PQLSX3lHD-EDEjpMAl44LRM7SgRS7nqhLnaEGqXGDOaHGJrmI8EEKLsiIL9LM27eh0Mt4pm715C3q0KmRb43Q3GBcfs1W26wIArn0_eAcuZbUfB2vcd_YRfPLa22zTD9ZPx4rhdfC9V9ZONgXTQ-omG41VDq7RRatshJu_XKLPp82ufsHb9-fXerXFmkmW8J7CnpWtBEGEJKosiNJCEPjiQgsNSsqWqYILDloxDSA0z0teMFXJfS4J5EuET7s6-BgDtM0wH1Fhaihpjqaa2BxNNSdTM3934lNnoIfm4Mcw24j_4L9eYGwJ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Bifunctional Molecular Linchpins: A Three-Component Coupling Protocol Employing 2-Bromoallyltrimethylsilane</title><source>Thieme Connect Journals</source><creator>Smith III, Amos B. ; Duffey, Matthew O.</creator><creatorcontrib>Smith III, Amos B. ; Duffey, Matthew O.</creatorcontrib><description>ABSTRACT
A new three-component coupling protocol, exploiting 2-bromoallyltrimethylsilane as a bifunctional linchpin, has been developed. The reaction sequence entails the following steps: lithiation of the vinyl bromide, addition of an aromatic or aliphatic aldehyde, execution of a solvent controlled 1,4-Brook rearrangement induced by HMPA to generate an allyl anion, and addition of a reactive second electrophile. Yields are moderate to good.</description><identifier>ISSN: 0936-5214</identifier><identifier>EISSN: 1437-2096</identifier><identifier>DOI: 10.1055/s-2004-825621</identifier><language>eng</language><subject>letter</subject><ispartof>Synlett, 2004-07, Vol.2004 (8), p.1363-1366</ispartof><rights>Georg Thieme Verlag Stuttgart · New York</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c272t-b1eb28f7e60670a840ac660ed56c6cea77f2a4565eca2cee6c538542a97b370e3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2004-825621.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2004-825621$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Smith III, Amos B.</creatorcontrib><creatorcontrib>Duffey, Matthew O.</creatorcontrib><title>Bifunctional Molecular Linchpins: A Three-Component Coupling Protocol Employing 2-Bromoallyltrimethylsilane</title><title>Synlett</title><addtitle>Synlett</addtitle><description>ABSTRACT
A new three-component coupling protocol, exploiting 2-bromoallyltrimethylsilane as a bifunctional linchpin, has been developed. The reaction sequence entails the following steps: lithiation of the vinyl bromide, addition of an aromatic or aliphatic aldehyde, execution of a solvent controlled 1,4-Brook rearrangement induced by HMPA to generate an allyl anion, and addition of a reactive second electrophile. Yields are moderate to good.</description><subject>letter</subject><issn>0936-5214</issn><issn>1437-2096</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNp1kL1OwzAYRS0EEqUwsucBMNhObCdsbVR-pCIYyhy55gtxcezIdoa8PanKynSlq6Orq4PQLSX3lHD-EDEjpMAl44LRM7SgRS7nqhLnaEGqXGDOaHGJrmI8EEKLsiIL9LM27eh0Mt4pm715C3q0KmRb43Q3GBcfs1W26wIArn0_eAcuZbUfB2vcd_YRfPLa22zTD9ZPx4rhdfC9V9ZONgXTQ-omG41VDq7RRatshJu_XKLPp82ufsHb9-fXerXFmkmW8J7CnpWtBEGEJKosiNJCEPjiQgsNSsqWqYILDloxDSA0z0teMFXJfS4J5EuET7s6-BgDtM0wH1Fhaihpjqaa2BxNNSdTM3934lNnoIfm4Mcw24j_4L9eYGwJ</recordid><startdate>20040701</startdate><enddate>20040701</enddate><creator>Smith III, Amos B.</creator><creator>Duffey, Matthew O.</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20040701</creationdate><title>Bifunctional Molecular Linchpins: A Three-Component Coupling Protocol Employing 2-Bromoallyltrimethylsilane</title><author>Smith III, Amos B. ; Duffey, Matthew O.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c272t-b1eb28f7e60670a840ac660ed56c6cea77f2a4565eca2cee6c538542a97b370e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>letter</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Smith III, Amos B.</creatorcontrib><creatorcontrib>Duffey, Matthew O.</creatorcontrib><collection>CrossRef</collection><jtitle>Synlett</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Smith III, Amos B.</au><au>Duffey, Matthew O.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bifunctional Molecular Linchpins: A Three-Component Coupling Protocol Employing 2-Bromoallyltrimethylsilane</atitle><jtitle>Synlett</jtitle><addtitle>Synlett</addtitle><date>2004-07-01</date><risdate>2004</risdate><volume>2004</volume><issue>8</issue><spage>1363</spage><epage>1366</epage><pages>1363-1366</pages><issn>0936-5214</issn><eissn>1437-2096</eissn><abstract>ABSTRACT
A new three-component coupling protocol, exploiting 2-bromoallyltrimethylsilane as a bifunctional linchpin, has been developed. The reaction sequence entails the following steps: lithiation of the vinyl bromide, addition of an aromatic or aliphatic aldehyde, execution of a solvent controlled 1,4-Brook rearrangement induced by HMPA to generate an allyl anion, and addition of a reactive second electrophile. Yields are moderate to good.</abstract><doi>10.1055/s-2004-825621</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0936-5214 |
| ispartof | Synlett, 2004-07, Vol.2004 (8), p.1363-1366 |
| issn | 0936-5214 1437-2096 |
| language | eng |
| recordid | cdi_crossref_primary_10_1055_s_2004_825621 |
| source | Thieme Connect Journals |
| subjects | letter |
| title | Bifunctional Molecular Linchpins: A Three-Component Coupling Protocol Employing 2-Bromoallyltrimethylsilane |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-21T16%3A29%3A51IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-thieme_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Bifunctional%20Molecular%20Linchpins:%20A%20Three-Component%20Coupling%20Protocol%20Employing%202-Bromoallyltrimethylsilane&rft.jtitle=Synlett&rft.au=Smith%20III,%20Amos%20B.&rft.date=2004-07-01&rft.volume=2004&rft.issue=8&rft.spage=1363&rft.epage=1366&rft.pages=1363-1366&rft.issn=0936-5214&rft.eissn=1437-2096&rft_id=info:doi/10.1055/s-2004-825621&rft_dat=%3Cthieme_cross%3E10_1055_s_2004_825621%3C/thieme_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/&rfr_iscdi=true |