One‐Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions
Organoaluminum‐mediated double interrupted Nazarov cyclization to access bicyclo[3.1.0]hexanols via nucleophilic methyl attack followed by Simmons–Smith‐type electrophilic cyclopropanation is reported. These alcohols can undergo ring opening to afford cyclohexanones or cyclohexenones, broadening the...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2018-04, Vol.24 (23), p.6052-6056 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 6056 |
|---|---|
| container_issue | 23 |
| container_start_page | 6052 |
| container_title | Chemistry : a European journal |
| container_volume | 24 |
| creator | Gelozia, Shorena Kwon, Yonghoon McDonald, Robert West, F. G. |
| description | Organoaluminum‐mediated double interrupted Nazarov cyclization to access bicyclo[3.1.0]hexanols via nucleophilic methyl attack followed by Simmons–Smith‐type electrophilic cyclopropanation is reported. These alcohols can undergo ring opening to afford cyclohexanones or cyclohexenones, broadening the range of scaffolds available via interrupted Nazarov reaction beyond the usual cyclopentanoid products. Throughout the sequence, a total of four new C−C bonds are formed, along with four new stereogenic centers.
Nazarov meets Simmons–Smith: AlMe3 has three roles—dienone Lewis acid activation, nucleophilic methyl transfer, and Simmons–Smith cyclopropanation, furnishing bicyclo[3.1.0]‐hexanols that can undergo subsequent reorganization. |
| doi_str_mv | 10.1002/chem.201800758 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2002484016</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2002484016</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4538-d91352be524570ac38a4a9b1c6a2e1fbbd7a6a5090dbc88f9b3c3b915fa2cf933</originalsourceid><addsrcrecordid>eNqFkMtKxDAUhoMoOF62rgNu3LTm0rTNUsdxFLwhuhIpSXrKdOgkY9Kq48pH8Bl9EjuMKLhxdeCc7_85fAjtURJTQtihmcAsZoTmhGQiX0MDKhiNeJaKdTQgMsmiVHC5ibZCmBJCZMr5ANXXFj7fP25ci8dgwau2dha7Ch_XZmEa98BjGpPHCbwq65qAlS3xcHlYbSwErBf4xHW6AXxuW_C-m7dQ4iv1prx7xregzLIz7KCNSjUBdr_nNro_Hd0Nz6KL6_H58OgiMongeVRKygXTIFgiMqIMz1WipKYmVQxopXWZqVQJIkmpTZ5XUnPDtaSiUsxUkvNtdLDqnXv31EFoi1kdDDSNsuC6ULDeVZInhKY9uv8HnbrO2_67nmK9RMm47Kl4RRnvQvBQFXNfz5RfFJQUS_PF0nzxY74PyFXgpW5g8Q9dDM9Gl7_ZL5ILiPs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2027589239</pqid></control><display><type>article</type><title>One‐Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Gelozia, Shorena ; Kwon, Yonghoon ; McDonald, Robert ; West, F. G.</creator><creatorcontrib>Gelozia, Shorena ; Kwon, Yonghoon ; McDonald, Robert ; West, F. G.</creatorcontrib><description>Organoaluminum‐mediated double interrupted Nazarov cyclization to access bicyclo[3.1.0]hexanols via nucleophilic methyl attack followed by Simmons–Smith‐type electrophilic cyclopropanation is reported. These alcohols can undergo ring opening to afford cyclohexanones or cyclohexenones, broadening the range of scaffolds available via interrupted Nazarov reaction beyond the usual cyclopentanoid products. Throughout the sequence, a total of four new C−C bonds are formed, along with four new stereogenic centers.
Nazarov meets Simmons–Smith: AlMe3 has three roles—dienone Lewis acid activation, nucleophilic methyl transfer, and Simmons–Smith cyclopropanation, furnishing bicyclo[3.1.0]‐hexanols that can undergo subsequent reorganization.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201800758</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alcohols ; cascade process ; Chemistry ; Cyclohexanone ; electrocyclic reactions ; Nazarov reaction ; organoaluminium ; Ring opening ; Simmons–Smith cyclopropanation</subject><ispartof>Chemistry : a European journal, 2018-04, Vol.24 (23), p.6052-6056</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4538-d91352be524570ac38a4a9b1c6a2e1fbbd7a6a5090dbc88f9b3c3b915fa2cf933</citedby><cites>FETCH-LOGICAL-c4538-d91352be524570ac38a4a9b1c6a2e1fbbd7a6a5090dbc88f9b3c3b915fa2cf933</cites><orcidid>0000-0001-7419-2314</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201800758$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201800758$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Gelozia, Shorena</creatorcontrib><creatorcontrib>Kwon, Yonghoon</creatorcontrib><creatorcontrib>McDonald, Robert</creatorcontrib><creatorcontrib>West, F. G.</creatorcontrib><title>One‐Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions</title><title>Chemistry : a European journal</title><description>Organoaluminum‐mediated double interrupted Nazarov cyclization to access bicyclo[3.1.0]hexanols via nucleophilic methyl attack followed by Simmons–Smith‐type electrophilic cyclopropanation is reported. These alcohols can undergo ring opening to afford cyclohexanones or cyclohexenones, broadening the range of scaffolds available via interrupted Nazarov reaction beyond the usual cyclopentanoid products. Throughout the sequence, a total of four new C−C bonds are formed, along with four new stereogenic centers.
Nazarov meets Simmons–Smith: AlMe3 has three roles—dienone Lewis acid activation, nucleophilic methyl transfer, and Simmons–Smith cyclopropanation, furnishing bicyclo[3.1.0]‐hexanols that can undergo subsequent reorganization.</description><subject>Alcohols</subject><subject>cascade process</subject><subject>Chemistry</subject><subject>Cyclohexanone</subject><subject>electrocyclic reactions</subject><subject>Nazarov reaction</subject><subject>organoaluminium</subject><subject>Ring opening</subject><subject>Simmons–Smith cyclopropanation</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkMtKxDAUhoMoOF62rgNu3LTm0rTNUsdxFLwhuhIpSXrKdOgkY9Kq48pH8Bl9EjuMKLhxdeCc7_85fAjtURJTQtihmcAsZoTmhGQiX0MDKhiNeJaKdTQgMsmiVHC5ibZCmBJCZMr5ANXXFj7fP25ci8dgwau2dha7Ch_XZmEa98BjGpPHCbwq65qAlS3xcHlYbSwErBf4xHW6AXxuW_C-m7dQ4iv1prx7xregzLIz7KCNSjUBdr_nNro_Hd0Nz6KL6_H58OgiMongeVRKygXTIFgiMqIMz1WipKYmVQxopXWZqVQJIkmpTZ5XUnPDtaSiUsxUkvNtdLDqnXv31EFoi1kdDDSNsuC6ULDeVZInhKY9uv8HnbrO2_67nmK9RMm47Kl4RRnvQvBQFXNfz5RfFJQUS_PF0nzxY74PyFXgpW5g8Q9dDM9Gl7_ZL5ILiPs</recordid><startdate>20180420</startdate><enddate>20180420</enddate><creator>Gelozia, Shorena</creator><creator>Kwon, Yonghoon</creator><creator>McDonald, Robert</creator><creator>West, F. G.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7419-2314</orcidid></search><sort><creationdate>20180420</creationdate><title>One‐Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions</title><author>Gelozia, Shorena ; Kwon, Yonghoon ; McDonald, Robert ; West, F. G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4538-d91352be524570ac38a4a9b1c6a2e1fbbd7a6a5090dbc88f9b3c3b915fa2cf933</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alcohols</topic><topic>cascade process</topic><topic>Chemistry</topic><topic>Cyclohexanone</topic><topic>electrocyclic reactions</topic><topic>Nazarov reaction</topic><topic>organoaluminium</topic><topic>Ring opening</topic><topic>Simmons–Smith cyclopropanation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gelozia, Shorena</creatorcontrib><creatorcontrib>Kwon, Yonghoon</creatorcontrib><creatorcontrib>McDonald, Robert</creatorcontrib><creatorcontrib>West, F. G.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gelozia, Shorena</au><au>Kwon, Yonghoon</au><au>McDonald, Robert</au><au>West, F. G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One‐Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions</atitle><jtitle>Chemistry : a European journal</jtitle><date>2018-04-20</date><risdate>2018</risdate><volume>24</volume><issue>23</issue><spage>6052</spage><epage>6056</epage><pages>6052-6056</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Organoaluminum‐mediated double interrupted Nazarov cyclization to access bicyclo[3.1.0]hexanols via nucleophilic methyl attack followed by Simmons–Smith‐type electrophilic cyclopropanation is reported. These alcohols can undergo ring opening to afford cyclohexanones or cyclohexenones, broadening the range of scaffolds available via interrupted Nazarov reaction beyond the usual cyclopentanoid products. Throughout the sequence, a total of four new C−C bonds are formed, along with four new stereogenic centers.
Nazarov meets Simmons–Smith: AlMe3 has three roles—dienone Lewis acid activation, nucleophilic methyl transfer, and Simmons–Smith cyclopropanation, furnishing bicyclo[3.1.0]‐hexanols that can undergo subsequent reorganization.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/chem.201800758</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-7419-2314</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2018-04, Vol.24 (23), p.6052-6056 |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2002484016 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alcohols cascade process Chemistry Cyclohexanone electrocyclic reactions Nazarov reaction organoaluminium Ring opening Simmons–Smith cyclopropanation |
| title | One‐Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-08T09%3A24%3A38IST&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=One%E2%80%90Pot%20Generation%20of%20Bicyclo%5B3.1.0%5Dhexanols%20and%20Cyclohexanones%20by%20Double%20Interrupted%20Nazarov%20Reactions&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Gelozia,%20Shorena&rft.date=2018-04-20&rft.volume=24&rft.issue=23&rft.spage=6052&rft.epage=6056&rft.pages=6052-6056&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.201800758&rft_dat=%3Cproquest_cross%3E2002484016%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=2027589239&rft_id=info:pmid/&rfr_iscdi=true |