Enantioselective Rh-Catalyzed Carboacylation of CN Bonds via C–C Activation of Benzocyclobutenones
Herein we describe the first enantioselective Rh-catalyzed carboacylation of oximes (imines) via C–C activation. In this transformation, the benzocyclobutenone C1–C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh–C bonds add across a CN bond, wh...
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| Veröffentlicht in: | Journal of the American Chemical Society 2016-01, Vol.138 (1), p.369-374 |
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| container_title | Journal of the American Chemical Society |
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| creator | Deng, Lin Xu, Tao Li, Hongbo Dong, Guangbin |
| description | Herein we describe the first enantioselective Rh-catalyzed carboacylation of oximes (imines) via C–C activation. In this transformation, the benzocyclobutenone C1–C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh–C bonds add across a CN bond, which provides a unique approach to access chiral lactams. A range of polycyclic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles. |
| doi_str_mv | 10.1021/jacs.5b11120 |
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In this transformation, the benzocyclobutenone C1–C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh–C bonds add across a CN bond, which provides a unique approach to access chiral lactams. A range of polycyclic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles.</description><identifier>ISSN: 0002-7863</identifier><identifier>ISSN: 1520-5126</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/jacs.5b11120</identifier><identifier>PMID: 26674855</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; catalysts ; Cyclization ; Cyclobutanes - chemistry ; derivatization ; enantiomers ; lactams ; oximes ; rhodium ; Rhodium - chemistry ; Stereoisomerism</subject><ispartof>Journal of the American Chemical Society, 2016-01, Vol.138 (1), p.369-374</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a516t-cbc3b95ea55d8bd745b590d1cec78b709e3db1669df277a91f0577f9d95df82e3</citedby><cites>FETCH-LOGICAL-a516t-cbc3b95ea55d8bd745b590d1cec78b709e3db1669df277a91f0577f9d95df82e3</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/jacs.5b11120$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jacs.5b11120$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26674855$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Deng, Lin</creatorcontrib><creatorcontrib>Xu, Tao</creatorcontrib><creatorcontrib>Li, Hongbo</creatorcontrib><creatorcontrib>Dong, Guangbin</creatorcontrib><title>Enantioselective Rh-Catalyzed Carboacylation of CN Bonds via C–C Activation of Benzocyclobutenones</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Herein we describe the first enantioselective Rh-catalyzed carboacylation of oximes (imines) via C–C activation. In this transformation, the benzocyclobutenone C1–C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh–C bonds add across a CN bond, which provides a unique approach to access chiral lactams. A range of polycyclic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles.</description><subject>Catalysis</subject><subject>catalysts</subject><subject>Cyclization</subject><subject>Cyclobutanes - chemistry</subject><subject>derivatization</subject><subject>enantiomers</subject><subject>lactams</subject><subject>oximes</subject><subject>rhodium</subject><subject>Rhodium - chemistry</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtq3EAQhhuTEE_s7LIOWmYROV0t9UObgC2cOGBiCM666UfJ1qDpdtTSwHiVO3jhw_g2PkDOYA2ejB0IZFUU9dVfj5-Qt0APgDL4ODcuHXALAIzukBlwRnMOTLwgM0opy6USxS55ndJ8Skum4BXZZULIUnE-IxfHwYShjQk7dEO7xOz7ZV6bwXSra_RZbXobjVt1ZmJCFpus_n179y07isGnbNmarL7_dVNnh-veLXOE4Tq6leuiHQcMMWDaJy8b0yV8s4l75Mfn4_P6JD89-_K1PjzNDQcx5M66wlYcDedeWS9LbnlFPTh0UllJKyy8BSEq3zApTQUN5VI2la-4bxTDYo98etS9Gu0CvcMw9KbTV327MP1KR9PqvyuhvdQXcalLpUrBxSTwfiPQx58jpkEv2uSw60zAOCbNpi8WQJWE_6IgBVUTCHxCPzyiro8p9dhsNwKq1zbqtY16Y-OEv3t-xRb-49vT6HXXPI59mJ76b60H7PmqFQ</recordid><startdate>20160113</startdate><enddate>20160113</enddate><creator>Deng, Lin</creator><creator>Xu, Tao</creator><creator>Li, Hongbo</creator><creator>Dong, Guangbin</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><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20160113</creationdate><title>Enantioselective Rh-Catalyzed Carboacylation of CN Bonds via C–C Activation of Benzocyclobutenones</title><author>Deng, Lin ; Xu, Tao ; Li, Hongbo ; Dong, Guangbin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a516t-cbc3b95ea55d8bd745b590d1cec78b709e3db1669df277a91f0577f9d95df82e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Catalysis</topic><topic>catalysts</topic><topic>Cyclization</topic><topic>Cyclobutanes - chemistry</topic><topic>derivatization</topic><topic>enantiomers</topic><topic>lactams</topic><topic>oximes</topic><topic>rhodium</topic><topic>Rhodium - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Deng, Lin</creatorcontrib><creatorcontrib>Xu, Tao</creatorcontrib><creatorcontrib>Li, Hongbo</creatorcontrib><creatorcontrib>Dong, Guangbin</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><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Deng, Lin</au><au>Xu, Tao</au><au>Li, Hongbo</au><au>Dong, Guangbin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Rh-Catalyzed Carboacylation of CN Bonds via C–C Activation of Benzocyclobutenones</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2016-01-13</date><risdate>2016</risdate><volume>138</volume><issue>1</issue><spage>369</spage><epage>374</epage><pages>369-374</pages><issn>0002-7863</issn><issn>1520-5126</issn><eissn>1520-5126</eissn><abstract>Herein we describe the first enantioselective Rh-catalyzed carboacylation of oximes (imines) via C–C activation. In this transformation, the benzocyclobutenone C1–C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh–C bonds add across a CN bond, which provides a unique approach to access chiral lactams. A range of polycyclic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26674855</pmid><doi>10.1021/jacs.5b11120</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | Catalysis catalysts Cyclization Cyclobutanes - chemistry derivatization enantiomers lactams oximes rhodium Rhodium - chemistry Stereoisomerism |
| title | Enantioselective Rh-Catalyzed Carboacylation of CN Bonds via C–C Activation of Benzocyclobutenones |
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