Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes
An N,N′‐dioxide/scandium(III) complex catalyzed, highly efficient conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields (up to 99 %) with good d.r. (up to 95/5) and excellent ee values (97 %–99 %). Moreover, the produc...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-01, Vol.55 (5), p.1859-1863 |
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| creator | Yao, Qian Liao, Yuting Lin, Lili Lin, Xiaobin Ji, Jie Liu, Xiaohua Feng, Xiaoming |
| description | An N,N′‐dioxide/scandium(III) complex catalyzed, highly efficient conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields (up to 99 %) with good d.r. (up to 95/5) and excellent ee values (97 %–99 %). Moreover, the products could be easily transformed into chiral furan and 5‐hydroxypyrazoline derivatives, both of which are important skeletons of many biologically active compounds and pharmacologicals.
An N,N′‐dioxide/ScIII complex catalyzed conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields with good d.r. and excellent ee values. Moreover, the products could be easily transformed to pharmacologically important chiral furan and 5‐hydroxypyrazoline derivatives. |
| doi_str_mv | 10.1002/anie.201509455 |
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An N,N′‐dioxide/ScIII complex catalyzed conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields with good d.r. and excellent ee values. Moreover, the products could be easily transformed to pharmacologically important chiral furan and 5‐hydroxypyrazoline derivatives.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201509455</identifier><identifier>PMID: 26694204</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>1,2-allenyl ketones ; 2-allenyl ketones ; 5-hydroxypyrazoline ; asymmetric catalysis ; Bioactive compounds ; Biological activity ; Catalysis ; Chemical synthesis ; Communication ; Communications ; enyne addition ; Esters ; furans ; Ketones ; Pharmacology ; Scandium</subject><ispartof>Angewandte Chemie International Edition, 2016-01, Vol.55 (5), p.1859-1863</ispartof><rights>2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c7075-535623a957f9e00ec505a45d23f400cd9927c4beacc2f0e201830eec8db30cfe3</citedby><cites>FETCH-LOGICAL-c7075-535623a957f9e00ec505a45d23f400cd9927c4beacc2f0e201830eec8db30cfe3</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%2Fanie.201509455$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201509455$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26694204$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yao, Qian</creatorcontrib><creatorcontrib>Liao, Yuting</creatorcontrib><creatorcontrib>Lin, Lili</creatorcontrib><creatorcontrib>Lin, Xiaobin</creatorcontrib><creatorcontrib>Ji, Jie</creatorcontrib><creatorcontrib>Liu, Xiaohua</creatorcontrib><creatorcontrib>Feng, Xiaoming</creatorcontrib><title>Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>An N,N′‐dioxide/scandium(III) complex catalyzed, highly efficient conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields (up to 99 %) with good d.r. (up to 95/5) and excellent ee values (97 %–99 %). Moreover, the products could be easily transformed into chiral furan and 5‐hydroxypyrazoline derivatives, both of which are important skeletons of many biologically active compounds and pharmacologicals.
An N,N′‐dioxide/ScIII complex catalyzed conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields with good d.r. and excellent ee values. Moreover, the products could be easily transformed to pharmacologically important chiral furan and 5‐hydroxypyrazoline derivatives.</description><subject>1,2-allenyl ketones</subject><subject>2-allenyl ketones</subject><subject>5-hydroxypyrazoline</subject><subject>asymmetric catalysis</subject><subject>Bioactive compounds</subject><subject>Biological activity</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Communication</subject><subject>Communications</subject><subject>enyne addition</subject><subject>Esters</subject><subject>furans</subject><subject>Ketones</subject><subject>Pharmacology</subject><subject>Scandium</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkk1vEzEQhlcIREvhyhFZ4sKBDf5c716Qoij9UENBoqhHy_HONg4bu7W9tPsL-Ns4SokKBzh5JD_zyK9niuI1wROCMf2gnYUJxUTghgvxpDgkgpKSScme5pozVspakIPiRYzrzNc1rp4XB7SqGk4xPyx-zrvOGgsuoa-jSyuINiLfodnKBt2jy2DjsIzJpiFBi8h7Wk77HtzYo3NI3kFEyxHNdNL9mKxB0zhuNpBCLmferYdrnQBN29Ym693W-0n33uXbeUwQIkoezd2YNS-LZ53uI7x6OI-Kb8fzy9lpufh8cjabLkojsRSlYKKiTDdCdg1gDEZgobloKes4xqZtGioNX4I2hnYY8sfUDAOYul0ybDpgR8XHnfdmWG6gNTl4zqlugt3oMCqvrfrzxtmVuvY_FJes5phkwbsHQfC3A8SkNjYa6HvtwA9REVnhhlSUsoy-_Qtd-yG4HE-RhnDOMWuaf1JS1BXBFeOZmuwoE3yMAbr9kwlW201Q201Q-03IDW8eB93jv0efgWYH3Nkexv_o1PTibP5YXu56bR7j_b5Xh--qkkwKdXVxoo4F_3J1Xp-qBfsF7pjQVg</recordid><startdate>20160126</startdate><enddate>20160126</enddate><creator>Yao, Qian</creator><creator>Liao, Yuting</creator><creator>Lin, Lili</creator><creator>Lin, Xiaobin</creator><creator>Ji, Jie</creator><creator>Liu, Xiaohua</creator><creator>Feng, Xiaoming</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>BSCLL</scope><scope>24P</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20160126</creationdate><title>Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes</title><author>Yao, Qian ; Liao, Yuting ; Lin, Lili ; Lin, Xiaobin ; Ji, Jie ; Liu, Xiaohua ; Feng, Xiaoming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c7075-535623a957f9e00ec505a45d23f400cd9927c4beacc2f0e201830eec8db30cfe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>1,2-allenyl ketones</topic><topic>2-allenyl ketones</topic><topic>5-hydroxypyrazoline</topic><topic>asymmetric catalysis</topic><topic>Bioactive compounds</topic><topic>Biological activity</topic><topic>Catalysis</topic><topic>Chemical synthesis</topic><topic>Communication</topic><topic>Communications</topic><topic>enyne addition</topic><topic>Esters</topic><topic>furans</topic><topic>Ketones</topic><topic>Pharmacology</topic><topic>Scandium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yao, Qian</creatorcontrib><creatorcontrib>Liao, Yuting</creatorcontrib><creatorcontrib>Lin, Lili</creatorcontrib><creatorcontrib>Lin, Xiaobin</creatorcontrib><creatorcontrib>Ji, Jie</creatorcontrib><creatorcontrib>Liu, Xiaohua</creatorcontrib><creatorcontrib>Feng, Xiaoming</creatorcontrib><collection>Istex</collection><collection>Wiley Online Library Open Access</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yao, Qian</au><au>Liao, Yuting</au><au>Lin, Lili</au><au>Lin, Xiaobin</au><au>Ji, Jie</au><au>Liu, Xiaohua</au><au>Feng, Xiaoming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-01-26</date><risdate>2016</risdate><volume>55</volume><issue>5</issue><spage>1859</spage><epage>1863</epage><pages>1859-1863</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>An N,N′‐dioxide/scandium(III) complex catalyzed, highly efficient conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields (up to 99 %) with good d.r. (up to 95/5) and excellent ee values (97 %–99 %). Moreover, the products could be easily transformed into chiral furan and 5‐hydroxypyrazoline derivatives, both of which are important skeletons of many biologically active compounds and pharmacologicals.
An N,N′‐dioxide/ScIII complex catalyzed conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields with good d.r. and excellent ee values. Moreover, the products could be easily transformed to pharmacologically important chiral furan and 5‐hydroxypyrazoline derivatives.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26694204</pmid><doi>10.1002/anie.201509455</doi><tpages>5</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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| subjects | 1,2-allenyl ketones 2-allenyl ketones 5-hydroxypyrazoline asymmetric catalysis Bioactive compounds Biological activity Catalysis Chemical synthesis Communication Communications enyne addition Esters furans Ketones Pharmacology Scandium |
| title | Efficient Synthesis of Chiral Trisubstituted 1,2-Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes |
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