Synthesis of 3-Oxa- and 3-Azabicyclo[4.1.0]heptanes by Gold-Catalyzed Cycloisomerization of Cyclopropenes

Synthesis of 3-Oxa- and 3-Azabicyclo[4.1.0]heptanes by Gold-Catalyzed Cycloisomerization of Cyclopropenes

Allyl 3,3-dimethylcyclopropenylcarbinyl ethers or sulfonamides undergo gold-catalyzed cycloisomerization leading to 5-isopropylidene-3-oxa- and 3-azabicyclo[4.1.0]heptanes in excellent yields and with high diastereoselectivities. These reactions constitute the first examples of intramolecular cyclop...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2010-09, Vol.12 (18), p.4144-4147
Hauptverfasser: Miege, Frédéric, Meyer, Christophe, Cossy, Janine
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4147
container_issue 18
container_start_page 4144
container_title Organic letters
container_volume 12
creator Miege, Frédéric
Meyer, Christophe
Cossy, Janine
description Allyl 3,3-dimethylcyclopropenylcarbinyl ethers or sulfonamides undergo gold-catalyzed cycloisomerization leading to 5-isopropylidene-3-oxa- and 3-azabicyclo[4.1.0]heptanes in excellent yields and with high diastereoselectivities. These reactions constitute the first examples of intramolecular cyclopropanation of an alkene by a gold carbene generated by electrophilic ring opening of a cyclopropene in the presence of gold(I) chloride.
doi_str_mv 10.1021/ol101741f
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_754030311</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>754030311</sourcerecordid><originalsourceid>FETCH-LOGICAL-a380t-64b7c5f4db4859a4781a971d4465eadaee743d67129377398898484b995e45923</originalsourceid><addsrcrecordid>eNptkDFPwzAQhS0EoqUw8AdQFoQYUuzYjuOxiqAgVeoATAhFl9hRXSVxiROJ9Nfj0tKJ6Z5O3727ewhdEzwlOCIPtiKYCEbKEzQmPKKhwDw6PeoYj9CFc2uMie_IczSKsIhiHrMxMq9D0620My6wZUDD5TeEATTKy9kWclMMRWU_2JRM8edKbzpotAvyIZjbSoUpdFANW62CdIcZZ2vdmi10xjY7u9_uprUb7acu0VkJldNXhzpB70-Pb-lzuFjOX9LZIgSa4C6MWS4KXjKVs4RLYCIhIAVRjMVcgwKtBaMqFiSSVAgqk0QmLGG5lFwzLiM6QXd7X7_4q9euy2rjCl1V_nTbu0xwhimmhHjyfk8WrXWu1WW2aU0N7ZARnO2CzY7Bevbm4NrntVZH8i9JD9zuAShctrZ92_gn_zH6AdxifZM</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>754030311</pqid></control><display><type>article</type><title>Synthesis of 3-Oxa- and 3-Azabicyclo[4.1.0]heptanes by Gold-Catalyzed Cycloisomerization of Cyclopropenes</title><source>ACS Publications</source><creator>Miege, Frédéric ; Meyer, Christophe ; Cossy, Janine</creator><creatorcontrib>Miege, Frédéric ; Meyer, Christophe ; Cossy, Janine</creatorcontrib><description>Allyl 3,3-dimethylcyclopropenylcarbinyl ethers or sulfonamides undergo gold-catalyzed cycloisomerization leading to 5-isopropylidene-3-oxa- and 3-azabicyclo[4.1.0]heptanes in excellent yields and with high diastereoselectivities. These reactions constitute the first examples of intramolecular cyclopropanation of an alkene by a gold carbene generated by electrophilic ring opening of a cyclopropene in the presence of gold(I) chloride.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol101741f</identifier><identifier>PMID: 20726564</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2010-09, Vol.12 (18), p.4144-4147</ispartof><rights>Copyright © 2010 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a380t-64b7c5f4db4859a4781a971d4465eadaee743d67129377398898484b995e45923</citedby><cites>FETCH-LOGICAL-a380t-64b7c5f4db4859a4781a971d4465eadaee743d67129377398898484b995e45923</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/ol101741f$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol101741f$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20726564$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Miege, Frédéric</creatorcontrib><creatorcontrib>Meyer, Christophe</creatorcontrib><creatorcontrib>Cossy, Janine</creatorcontrib><title>Synthesis of 3-Oxa- and 3-Azabicyclo[4.1.0]heptanes by Gold-Catalyzed Cycloisomerization of Cyclopropenes</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Allyl 3,3-dimethylcyclopropenylcarbinyl ethers or sulfonamides undergo gold-catalyzed cycloisomerization leading to 5-isopropylidene-3-oxa- and 3-azabicyclo[4.1.0]heptanes in excellent yields and with high diastereoselectivities. These reactions constitute the first examples of intramolecular cyclopropanation of an alkene by a gold carbene generated by electrophilic ring opening of a cyclopropene in the presence of gold(I) chloride.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNptkDFPwzAQhS0EoqUw8AdQFoQYUuzYjuOxiqAgVeoATAhFl9hRXSVxiROJ9Nfj0tKJ6Z5O3727ewhdEzwlOCIPtiKYCEbKEzQmPKKhwDw6PeoYj9CFc2uMie_IczSKsIhiHrMxMq9D0620My6wZUDD5TeEATTKy9kWclMMRWU_2JRM8edKbzpotAvyIZjbSoUpdFANW62CdIcZZ2vdmi10xjY7u9_uprUb7acu0VkJldNXhzpB70-Pb-lzuFjOX9LZIgSa4C6MWS4KXjKVs4RLYCIhIAVRjMVcgwKtBaMqFiSSVAgqk0QmLGG5lFwzLiM6QXd7X7_4q9euy2rjCl1V_nTbu0xwhimmhHjyfk8WrXWu1WW2aU0N7ZARnO2CzY7Bevbm4NrntVZH8i9JD9zuAShctrZ92_gn_zH6AdxifZM</recordid><startdate>20100917</startdate><enddate>20100917</enddate><creator>Miege, Frédéric</creator><creator>Meyer, Christophe</creator><creator>Cossy, Janine</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20100917</creationdate><title>Synthesis of 3-Oxa- and 3-Azabicyclo[4.1.0]heptanes by Gold-Catalyzed Cycloisomerization of Cyclopropenes</title><author>Miege, Frédéric ; Meyer, Christophe ; Cossy, Janine</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-64b7c5f4db4859a4781a971d4465eadaee743d67129377398898484b995e45923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miege, Frédéric</creatorcontrib><creatorcontrib>Meyer, Christophe</creatorcontrib><creatorcontrib>Cossy, Janine</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>Miege, Frédéric</au><au>Meyer, Christophe</au><au>Cossy, Janine</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 3-Oxa- and 3-Azabicyclo[4.1.0]heptanes by Gold-Catalyzed Cycloisomerization of Cyclopropenes</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2010-09-17</date><risdate>2010</risdate><volume>12</volume><issue>18</issue><spage>4144</spage><epage>4147</epage><pages>4144-4147</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Allyl 3,3-dimethylcyclopropenylcarbinyl ethers or sulfonamides undergo gold-catalyzed cycloisomerization leading to 5-isopropylidene-3-oxa- and 3-azabicyclo[4.1.0]heptanes in excellent yields and with high diastereoselectivities. These reactions constitute the first examples of intramolecular cyclopropanation of an alkene by a gold carbene generated by electrophilic ring opening of a cyclopropene in the presence of gold(I) chloride.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20726564</pmid><doi>10.1021/ol101741f</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2010-09, Vol.12 (18), p.4144-4147
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_754030311
source ACS Publications
title Synthesis of 3-Oxa- and 3-Azabicyclo[4.1.0]heptanes by Gold-Catalyzed Cycloisomerization of Cyclopropenes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T20%3A36%3A03IST&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%20of%203-Oxa-%20and%203-Azabicyclo%5B4.1.0%5Dheptanes%20by%20Gold-Catalyzed%20Cycloisomerization%20of%20Cyclopropenes&rft.jtitle=Organic%20letters&rft.au=Miege,%20Fre%CC%81de%CC%81ric&rft.date=2010-09-17&rft.volume=12&rft.issue=18&rft.spage=4144&rft.epage=4147&rft.pages=4144-4147&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol101741f&rft_dat=%3Cproquest_cross%3E754030311%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=754030311&rft_id=info:pmid/20726564&rfr_iscdi=true