Rhodium-Catalyzed Intramolecular [3+2+2] Cycloadditions between Alkylidenecyclopropanes, Alkynes, and Alkenes
A Rh‐catalyzed intramolecular [3+2+2] cycloaddition is reported. The cycloaddition affords synthetically relevant 5,7,5‐fused tricyclic systems of type 2 from readily available dienyne precursors. The transformation takes place with moderate or good yields, high diastereoselectivity, and total chemo...
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| Veröffentlicht in: | Chemistry : a European journal 2014-08, Vol.20 (33), p.10255-10259 |
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| container_title | Chemistry : a European journal |
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| creator | Araya, Marisel Gulías, Moisés Fernández, Israel Bhargava, Gaurav Castedo, Luis Mascareñas, José Luis López, Fernando |
| description | A Rh‐catalyzed intramolecular [3+2+2] cycloaddition is reported. The cycloaddition affords synthetically relevant 5,7,5‐fused tricyclic systems of type 2 from readily available dienyne precursors. The transformation takes place with moderate or good yields, high diastereoselectivity, and total chemoselectivity.
Carbocycle synthesis: A Rh‐catalyzed intramolecular [3+2+2] cycloaddition is reported (see scheme; cod=1,5‐cyclooctadiene, EWG=electron‐withdrawing group). The cycloaddition affords synthetically relevant 5,7,5‐fused tricyclic systems of type 2 from readily available dienyne precursors. The transformation takes place with moderate or good yields, high diastereoselectivity, and total chemoselectivity. |
| doi_str_mv | 10.1002/chem.201402473 |
| format | Article |
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Carbocycle synthesis: A Rh‐catalyzed intramolecular [3+2+2] cycloaddition is reported (see scheme; cod=1,5‐cyclooctadiene, EWG=electron‐withdrawing group). The cycloaddition affords synthetically relevant 5,7,5‐fused tricyclic systems of type 2 from readily available dienyne precursors. The transformation takes place with moderate or good yields, high diastereoselectivity, and total chemoselectivity.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201402473</identifier><identifier>PMID: 25042880</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkenes ; Alkenes - chemistry ; alkylidenecyclopropane ; Alkynes ; Alkynes - chemistry ; carbocycles ; Catalysis ; Chemistry ; Cycloaddition ; Cycloaddition Reaction ; cycloadditions ; Cyclopropanes - chemistry ; Models, Molecular ; Precursors ; rhodium ; Rhodium - chemistry ; Stereoisomerism ; Synthesis ; Transformations</subject><ispartof>Chemistry : a European journal, 2014-08, Vol.20 (33), p.10255-10259</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5913-5595ddb8f536caf780a073d41569e179e6c20da4af32ab659ed2d16a37d0ac6e3</citedby><cites>FETCH-LOGICAL-c5913-5595ddb8f536caf780a073d41569e179e6c20da4af32ab659ed2d16a37d0ac6e3</cites></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.201402473$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201402473$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25042880$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Araya, Marisel</creatorcontrib><creatorcontrib>Gulías, Moisés</creatorcontrib><creatorcontrib>Fernández, Israel</creatorcontrib><creatorcontrib>Bhargava, Gaurav</creatorcontrib><creatorcontrib>Castedo, Luis</creatorcontrib><creatorcontrib>Mascareñas, José Luis</creatorcontrib><creatorcontrib>López, Fernando</creatorcontrib><title>Rhodium-Catalyzed Intramolecular [3+2+2] Cycloadditions between Alkylidenecyclopropanes, Alkynes, and Alkenes</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A Rh‐catalyzed intramolecular [3+2+2] cycloaddition is reported. The cycloaddition affords synthetically relevant 5,7,5‐fused tricyclic systems of type 2 from readily available dienyne precursors. The transformation takes place with moderate or good yields, high diastereoselectivity, and total chemoselectivity.
Carbocycle synthesis: A Rh‐catalyzed intramolecular [3+2+2] cycloaddition is reported (see scheme; cod=1,5‐cyclooctadiene, EWG=electron‐withdrawing group). The cycloaddition affords synthetically relevant 5,7,5‐fused tricyclic systems of type 2 from readily available dienyne precursors. The transformation takes place with moderate or good yields, high diastereoselectivity, and total chemoselectivity.</description><subject>Alkenes</subject><subject>Alkenes - chemistry</subject><subject>alkylidenecyclopropane</subject><subject>Alkynes</subject><subject>Alkynes - chemistry</subject><subject>carbocycles</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Cycloaddition</subject><subject>Cycloaddition Reaction</subject><subject>cycloadditions</subject><subject>Cyclopropanes - chemistry</subject><subject>Models, Molecular</subject><subject>Precursors</subject><subject>rhodium</subject><subject>Rhodium - chemistry</subject><subject>Stereoisomerism</subject><subject>Synthesis</subject><subject>Transformations</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkV1r1EAUhgdR7Fq99VIC3ght1vnImclctqFuC6uC-AUiw-zMCU07SdZMQht_vUm3LuJNr2aGed6Hc3gJecnoklHK37pLrJecsozyTIlHZMGAs1QoCY_JgupMpRKEPiDPYryilGopxFNywIFmPM_pgtSfLltfDXVa2N6G8Tf65KLpO1u3Ad0QbJf8EEf8iP9MitGF1npf9VXbxGSD_Q1ik5yE6zFUHht0M7Dt2q1tMB7ffdxdbOPnx0TE5-RJaUPEF_fnIfny7uxzcZ6uP64uipN16kAzkQJo8H6TlyCks6XKqaVK-IyB1MiURuk49TazpeB2I0Gj555JK5Sn1kkUh-TNzjuN82vA2Ju6ig5DmEZrh2iYmpwAMtcPowBMcJ1xNqGv_0Ov2qFrpkVmigoQkPGJWu4o17UxdliabVfVthsNo2buzMydmX1nU-DVvXbY1Oj3-N-SJkDvgJsq4PiAzhTnZ-__lae7bBV7vN1nbXdtpBIKzLcPK_N1lX0_XYM0QvwBq2GxmA</recordid><startdate>20140811</startdate><enddate>20140811</enddate><creator>Araya, Marisel</creator><creator>Gulías, Moisés</creator><creator>Fernández, Israel</creator><creator>Bhargava, Gaurav</creator><creator>Castedo, Luis</creator><creator>Mascareñas, José Luis</creator><creator>López, Fernando</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20140811</creationdate><title>Rhodium-Catalyzed Intramolecular [3+2+2] Cycloadditions between Alkylidenecyclopropanes, Alkynes, and Alkenes</title><author>Araya, Marisel ; Gulías, Moisés ; Fernández, Israel ; Bhargava, Gaurav ; Castedo, Luis ; Mascareñas, José Luis ; López, Fernando</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5913-5595ddb8f536caf780a073d41569e179e6c20da4af32ab659ed2d16a37d0ac6e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Alkenes</topic><topic>Alkenes - chemistry</topic><topic>alkylidenecyclopropane</topic><topic>Alkynes</topic><topic>Alkynes - chemistry</topic><topic>carbocycles</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Cycloaddition</topic><topic>Cycloaddition Reaction</topic><topic>cycloadditions</topic><topic>Cyclopropanes - chemistry</topic><topic>Models, Molecular</topic><topic>Precursors</topic><topic>rhodium</topic><topic>Rhodium - chemistry</topic><topic>Stereoisomerism</topic><topic>Synthesis</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Araya, Marisel</creatorcontrib><creatorcontrib>Gulías, Moisés</creatorcontrib><creatorcontrib>Fernández, Israel</creatorcontrib><creatorcontrib>Bhargava, Gaurav</creatorcontrib><creatorcontrib>Castedo, Luis</creatorcontrib><creatorcontrib>Mascareñas, José Luis</creatorcontrib><creatorcontrib>López, Fernando</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><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>Araya, Marisel</au><au>Gulías, Moisés</au><au>Fernández, Israel</au><au>Bhargava, Gaurav</au><au>Castedo, Luis</au><au>Mascareñas, José Luis</au><au>López, Fernando</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhodium-Catalyzed Intramolecular [3+2+2] Cycloadditions between Alkylidenecyclopropanes, Alkynes, and Alkenes</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. 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Carbocycle synthesis: A Rh‐catalyzed intramolecular [3+2+2] cycloaddition is reported (see scheme; cod=1,5‐cyclooctadiene, EWG=electron‐withdrawing group). The cycloaddition affords synthetically relevant 5,7,5‐fused tricyclic systems of type 2 from readily available dienyne precursors. The transformation takes place with moderate or good yields, high diastereoselectivity, and total chemoselectivity.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25042880</pmid><doi>10.1002/chem.201402473</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; Wiley Journals |
| subjects | Alkenes Alkenes - chemistry alkylidenecyclopropane Alkynes Alkynes - chemistry carbocycles Catalysis Chemistry Cycloaddition Cycloaddition Reaction cycloadditions Cyclopropanes - chemistry Models, Molecular Precursors rhodium Rhodium - chemistry Stereoisomerism Synthesis Transformations |
| title | Rhodium-Catalyzed Intramolecular [3+2+2] Cycloadditions between Alkylidenecyclopropanes, Alkynes, and Alkenes |
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