Straightforward Access to the [3.2.2]Nonatriene Structural Framework via Intramolecular Cyclopropenation/Buchner Reaction/Cope Rearrangement Cascade
A one-pot cascade process of benzyl enoldiazoacatates, initiated by dirhodium(II)-catalyzed intramolecular cyclopropene formation, occurs via a subsequent Buchner reaction and Cope rearrangement to provide straightforward access to bicyclo[3.2.2]nonatriene derivatives in high yields and selectivitie...
Gespeichert in:
Veröffentlicht in: | Organic letters 2015-02, Vol.17 (4), p.790-793 |
---|---|
Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 793 |
---|---|
container_issue | 4 |
container_start_page | 790 |
container_title | Organic letters |
container_volume | 17 |
creator | Xu, Xinfang Wang, Xiangbo Zavalij, Peter Y Doyle, Michael P |
description | A one-pot cascade process of benzyl enoldiazoacatates, initiated by dirhodium(II)-catalyzed intramolecular cyclopropene formation, occurs via a subsequent Buchner reaction and Cope rearrangement to provide straightforward access to bicyclo[3.2.2]nonatriene derivatives in high yields and selectivities. |
doi_str_mv | 10.1021/ol503498n |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1657317946</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1657317946</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-a1cd85bf6cc80524a638a9f160afc975728c5e8fe698fd1da765ba4398868ce83</originalsourceid><addsrcrecordid>eNptkc1O3DAQx60KVChw6AtUviDRwy52vHacI42gRUJFaumpQtHsZMKGJvbWdop4jz5wDUv3xGm-fvPXfDD2Xoq5FIU89YMWalFZ94btS12oWSl0sbP1jdhj72K8F0LmTPWW7RXaGGON2md_v6cA_d0qdT48QGj5GSLFyJPnaUX8p5oX8-L2q3eQQk-OeOYnTFOAgV8EGOnBh1_8Tw_80mWl0Q-E0wCB1484-HXwa8qtvXennyZcOQr8GwE-J-pce4pCAHdHI7nEa4gILR2y3Q6GSEcv9oD9uDi_qb_Mrq4_X9ZnVzNQVqYZSGytXnYG0eaFF2CUhaqTRkCHVanLwqIm25GpbNfKFkqjl7BQlbXGIll1wE42unnO3xPF1Ix9RBoGcOSn2EijSyXLamEy-nGDYvAxBuqadehHCI-NFM3TE5rtEzL74UV2Wo7Ubsn_V8_A8QYAjM29n4LLW74i9A9U5JEm</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1657317946</pqid></control><display><type>article</type><title>Straightforward Access to the [3.2.2]Nonatriene Structural Framework via Intramolecular Cyclopropenation/Buchner Reaction/Cope Rearrangement Cascade</title><source>MEDLINE</source><source>ACS Publications</source><creator>Xu, Xinfang ; Wang, Xiangbo ; Zavalij, Peter Y ; Doyle, Michael P</creator><creatorcontrib>Xu, Xinfang ; Wang, Xiangbo ; Zavalij, Peter Y ; Doyle, Michael P</creatorcontrib><description>A one-pot cascade process of benzyl enoldiazoacatates, initiated by dirhodium(II)-catalyzed intramolecular cyclopropene formation, occurs via a subsequent Buchner reaction and Cope rearrangement to provide straightforward access to bicyclo[3.2.2]nonatriene derivatives in high yields and selectivities.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol503498n</identifier><identifier>PMID: 25666863</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Benzyl Compounds - chemical synthesis ; Benzyl Compounds - chemistry ; Bridged Bicyclo Compounds - chemistry ; Catalysis ; Cycloparaffins - chemistry ; Cyclopropanes - chemistry ; Molecular Structure ; Rhodium - chemistry</subject><ispartof>Organic letters, 2015-02, Vol.17 (4), p.790-793</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-a1cd85bf6cc80524a638a9f160afc975728c5e8fe698fd1da765ba4398868ce83</citedby><cites>FETCH-LOGICAL-a381t-a1cd85bf6cc80524a638a9f160afc975728c5e8fe698fd1da765ba4398868ce83</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/ol503498n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol503498n$$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/25666863$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xu, Xinfang</creatorcontrib><creatorcontrib>Wang, Xiangbo</creatorcontrib><creatorcontrib>Zavalij, Peter Y</creatorcontrib><creatorcontrib>Doyle, Michael P</creatorcontrib><title>Straightforward Access to the [3.2.2]Nonatriene Structural Framework via Intramolecular Cyclopropenation/Buchner Reaction/Cope Rearrangement Cascade</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A one-pot cascade process of benzyl enoldiazoacatates, initiated by dirhodium(II)-catalyzed intramolecular cyclopropene formation, occurs via a subsequent Buchner reaction and Cope rearrangement to provide straightforward access to bicyclo[3.2.2]nonatriene derivatives in high yields and selectivities.</description><subject>Benzyl Compounds - chemical synthesis</subject><subject>Benzyl Compounds - chemistry</subject><subject>Bridged Bicyclo Compounds - chemistry</subject><subject>Catalysis</subject><subject>Cycloparaffins - chemistry</subject><subject>Cyclopropanes - chemistry</subject><subject>Molecular Structure</subject><subject>Rhodium - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1O3DAQx60KVChw6AtUviDRwy52vHacI42gRUJFaumpQtHsZMKGJvbWdop4jz5wDUv3xGm-fvPXfDD2Xoq5FIU89YMWalFZ94btS12oWSl0sbP1jdhj72K8F0LmTPWW7RXaGGON2md_v6cA_d0qdT48QGj5GSLFyJPnaUX8p5oX8-L2q3eQQk-OeOYnTFOAgV8EGOnBh1_8Tw_80mWl0Q-E0wCB1484-HXwa8qtvXennyZcOQr8GwE-J-pce4pCAHdHI7nEa4gILR2y3Q6GSEcv9oD9uDi_qb_Mrq4_X9ZnVzNQVqYZSGytXnYG0eaFF2CUhaqTRkCHVanLwqIm25GpbNfKFkqjl7BQlbXGIll1wE42unnO3xPF1Ix9RBoGcOSn2EijSyXLamEy-nGDYvAxBuqadehHCI-NFM3TE5rtEzL74UV2Wo7Ubsn_V8_A8QYAjM29n4LLW74i9A9U5JEm</recordid><startdate>20150220</startdate><enddate>20150220</enddate><creator>Xu, Xinfang</creator><creator>Wang, Xiangbo</creator><creator>Zavalij, Peter Y</creator><creator>Doyle, Michael P</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>20150220</creationdate><title>Straightforward Access to the [3.2.2]Nonatriene Structural Framework via Intramolecular Cyclopropenation/Buchner Reaction/Cope Rearrangement Cascade</title><author>Xu, Xinfang ; Wang, Xiangbo ; Zavalij, Peter Y ; Doyle, Michael P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-a1cd85bf6cc80524a638a9f160afc975728c5e8fe698fd1da765ba4398868ce83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Benzyl Compounds - chemical synthesis</topic><topic>Benzyl Compounds - chemistry</topic><topic>Bridged Bicyclo Compounds - chemistry</topic><topic>Catalysis</topic><topic>Cycloparaffins - chemistry</topic><topic>Cyclopropanes - chemistry</topic><topic>Molecular Structure</topic><topic>Rhodium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xu, Xinfang</creatorcontrib><creatorcontrib>Wang, Xiangbo</creatorcontrib><creatorcontrib>Zavalij, Peter Y</creatorcontrib><creatorcontrib>Doyle, Michael P</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>Xu, Xinfang</au><au>Wang, Xiangbo</au><au>Zavalij, Peter Y</au><au>Doyle, Michael P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Straightforward Access to the [3.2.2]Nonatriene Structural Framework via Intramolecular Cyclopropenation/Buchner Reaction/Cope Rearrangement Cascade</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2015-02-20</date><risdate>2015</risdate><volume>17</volume><issue>4</issue><spage>790</spage><epage>793</epage><pages>790-793</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A one-pot cascade process of benzyl enoldiazoacatates, initiated by dirhodium(II)-catalyzed intramolecular cyclopropene formation, occurs via a subsequent Buchner reaction and Cope rearrangement to provide straightforward access to bicyclo[3.2.2]nonatriene derivatives in high yields and selectivities.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25666863</pmid><doi>10.1021/ol503498n</doi><tpages>4</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1523-7060 |
ispartof | Organic letters, 2015-02, Vol.17 (4), p.790-793 |
issn | 1523-7060 1523-7052 |
language | eng |
recordid | cdi_proquest_miscellaneous_1657317946 |
source | MEDLINE; ACS Publications |
subjects | Benzyl Compounds - chemical synthesis Benzyl Compounds - chemistry Bridged Bicyclo Compounds - chemistry Catalysis Cycloparaffins - chemistry Cyclopropanes - chemistry Molecular Structure Rhodium - chemistry |
title | Straightforward Access to the [3.2.2]Nonatriene Structural Framework via Intramolecular Cyclopropenation/Buchner Reaction/Cope Rearrangement Cascade |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T10%3A53%3A05IST&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=Straightforward%20Access%20to%20the%20%5B3.2.2%5DNonatriene%20Structural%20Framework%20via%20Intramolecular%20Cyclopropenation/Buchner%20Reaction/Cope%20Rearrangement%20Cascade&rft.jtitle=Organic%20letters&rft.au=Xu,%20Xinfang&rft.date=2015-02-20&rft.volume=17&rft.issue=4&rft.spage=790&rft.epage=793&rft.pages=790-793&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol503498n&rft_dat=%3Cproquest_cross%3E1657317946%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=1657317946&rft_id=info:pmid/25666863&rfr_iscdi=true |