Asymmetric Vinylogous Michael Addition/Cyclization Cascade Reaction for the Construction of Diversely Structured Spiro- Oxindole Skeletons
We present the first organocatalytic asymmetric vinylogous Michael/cyclization reaction of α,α‐dicyanoalkenes with 3‐alkylideneoxindoles. A series of diversely structured spiro‐oxindole skeletons was smoothly delivered with excellent yields and stereoselectivity control (94–99% yields, >20:1 dr a...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2013-11, Vol.355 (16), p.3119-3123 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3123 |
|---|---|
| container_issue | 16 |
| container_start_page | 3119 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 355 |
| creator | Shi, Xiao-Mei Dong, Wei-Ping Zhu, Li-Ping Jiang, Xian-Xing Wang, Rui |
| description | We present the first organocatalytic asymmetric vinylogous Michael/cyclization reaction of α,α‐dicyanoalkenes with 3‐alkylideneoxindoles. A series of diversely structured spiro‐oxindole skeletons was smoothly delivered with excellent yields and stereoselectivity control (94–99% yields, >20:1 dr and 91 to >99% ee). |
| doi_str_mv | 10.1002/adsc.201300329 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744727591</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1494315575</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4309-22bd7422531c54a3495e195d571ae5abd227e2b9c8976cf2458c3271497e5653</originalsourceid><addsrcrecordid>eNqFkUtPGzEUhUdVkUop2669ZDPBz3G8jIbykCBIDQKJjeXYd4rBGaf2BBh-Ar-ahEERO1b36Oh8R7o6RfGb4BHBmB4al-2IYsIwZlR9K3ZJRUTJSaW-b7XAP4qfOd9jTORYyt3idZL7xQK65C269m0f4r-4yujC2zsDAU2c852P7WHd2-BfzEaj2mRrHKC_YOy70cSEujtAdWxzl1aDGRt05B8hZQg9mr3bqwQOzZY-xRJdPvvWxQBo9gABujX5q9hpTMiw_3H3iqvjP1f1aXl-eXJWT85LyxlWJaVzJzmlghEruGFcCSBKOCGJAWHmjlIJdK7sWMnKNpSLsWVUEq4kiEqwveJgqF2m-H8FudMLny2EYFpYv66J5FxSKRT5OsoVZ0QIuWkdDVGbYs4JGr1MfmFSrwnWm3n0Zh69nWcNqAF48gH6L9J6cjSrP7PlwPrcwfOWNelBV5JJoW-mJ3p6PL6-vZjeaMLeAFPkpNQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1494315575</pqid></control><display><type>article</type><title>Asymmetric Vinylogous Michael Addition/Cyclization Cascade Reaction for the Construction of Diversely Structured Spiro- Oxindole Skeletons</title><source>Wiley-Blackwell Journals</source><creator>Shi, Xiao-Mei ; Dong, Wei-Ping ; Zhu, Li-Ping ; Jiang, Xian-Xing ; Wang, Rui</creator><creatorcontrib>Shi, Xiao-Mei ; Dong, Wei-Ping ; Zhu, Li-Ping ; Jiang, Xian-Xing ; Wang, Rui</creatorcontrib><description>We present the first organocatalytic asymmetric vinylogous Michael/cyclization reaction of α,α‐dicyanoalkenes with 3‐alkylideneoxindoles. A series of diversely structured spiro‐oxindole skeletons was smoothly delivered with excellent yields and stereoselectivity control (94–99% yields, >20:1 dr and 91 to >99% ee).</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201300329</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>asymmetric catalysis ; Asymmetry ; cascade reactions ; Cascades ; Catalysis ; Construction ; dicyanoalkenes ; Michael addition ; Michael reaction ; organocatalysis ; Stereoselectivity ; Synthesis</subject><ispartof>Advanced synthesis & catalysis, 2013-11, Vol.355 (16), p.3119-3123</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4309-22bd7422531c54a3495e195d571ae5abd227e2b9c8976cf2458c3271497e5653</citedby><cites>FETCH-LOGICAL-c4309-22bd7422531c54a3495e195d571ae5abd227e2b9c8976cf2458c3271497e5653</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%2Fadsc.201300329$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201300329$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Shi, Xiao-Mei</creatorcontrib><creatorcontrib>Dong, Wei-Ping</creatorcontrib><creatorcontrib>Zhu, Li-Ping</creatorcontrib><creatorcontrib>Jiang, Xian-Xing</creatorcontrib><creatorcontrib>Wang, Rui</creatorcontrib><title>Asymmetric Vinylogous Michael Addition/Cyclization Cascade Reaction for the Construction of Diversely Structured Spiro- Oxindole Skeletons</title><title>Advanced synthesis & catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>We present the first organocatalytic asymmetric vinylogous Michael/cyclization reaction of α,α‐dicyanoalkenes with 3‐alkylideneoxindoles. A series of diversely structured spiro‐oxindole skeletons was smoothly delivered with excellent yields and stereoselectivity control (94–99% yields, >20:1 dr and 91 to >99% ee).</description><subject>asymmetric catalysis</subject><subject>Asymmetry</subject><subject>cascade reactions</subject><subject>Cascades</subject><subject>Catalysis</subject><subject>Construction</subject><subject>dicyanoalkenes</subject><subject>Michael addition</subject><subject>Michael reaction</subject><subject>organocatalysis</subject><subject>Stereoselectivity</subject><subject>Synthesis</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkUtPGzEUhUdVkUop2669ZDPBz3G8jIbykCBIDQKJjeXYd4rBGaf2BBh-Ar-ahEERO1b36Oh8R7o6RfGb4BHBmB4al-2IYsIwZlR9K3ZJRUTJSaW-b7XAP4qfOd9jTORYyt3idZL7xQK65C269m0f4r-4yujC2zsDAU2c852P7WHd2-BfzEaj2mRrHKC_YOy70cSEujtAdWxzl1aDGRt05B8hZQg9mr3bqwQOzZY-xRJdPvvWxQBo9gABujX5q9hpTMiw_3H3iqvjP1f1aXl-eXJWT85LyxlWJaVzJzmlghEruGFcCSBKOCGJAWHmjlIJdK7sWMnKNpSLsWVUEq4kiEqwveJgqF2m-H8FudMLny2EYFpYv66J5FxSKRT5OsoVZ0QIuWkdDVGbYs4JGr1MfmFSrwnWm3n0Zh69nWcNqAF48gH6L9J6cjSrP7PlwPrcwfOWNelBV5JJoW-mJ3p6PL6-vZjeaMLeAFPkpNQ</recordid><startdate>20131111</startdate><enddate>20131111</enddate><creator>Shi, Xiao-Mei</creator><creator>Dong, Wei-Ping</creator><creator>Zhu, Li-Ping</creator><creator>Jiang, Xian-Xing</creator><creator>Wang, Rui</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20131111</creationdate><title>Asymmetric Vinylogous Michael Addition/Cyclization Cascade Reaction for the Construction of Diversely Structured Spiro- Oxindole Skeletons</title><author>Shi, Xiao-Mei ; Dong, Wei-Ping ; Zhu, Li-Ping ; Jiang, Xian-Xing ; Wang, Rui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4309-22bd7422531c54a3495e195d571ae5abd227e2b9c8976cf2458c3271497e5653</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>asymmetric catalysis</topic><topic>Asymmetry</topic><topic>cascade reactions</topic><topic>Cascades</topic><topic>Catalysis</topic><topic>Construction</topic><topic>dicyanoalkenes</topic><topic>Michael addition</topic><topic>Michael reaction</topic><topic>organocatalysis</topic><topic>Stereoselectivity</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shi, Xiao-Mei</creatorcontrib><creatorcontrib>Dong, Wei-Ping</creatorcontrib><creatorcontrib>Zhu, Li-Ping</creatorcontrib><creatorcontrib>Jiang, Xian-Xing</creatorcontrib><creatorcontrib>Wang, Rui</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shi, Xiao-Mei</au><au>Dong, Wei-Ping</au><au>Zhu, Li-Ping</au><au>Jiang, Xian-Xing</au><au>Wang, Rui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Vinylogous Michael Addition/Cyclization Cascade Reaction for the Construction of Diversely Structured Spiro- Oxindole Skeletons</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2013-11-11</date><risdate>2013</risdate><volume>355</volume><issue>16</issue><spage>3119</spage><epage>3123</epage><pages>3119-3123</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>We present the first organocatalytic asymmetric vinylogous Michael/cyclization reaction of α,α‐dicyanoalkenes with 3‐alkylideneoxindoles. A series of diversely structured spiro‐oxindole skeletons was smoothly delivered with excellent yields and stereoselectivity control (94–99% yields, >20:1 dr and 91 to >99% ee).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201300329</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2013-11, Vol.355 (16), p.3119-3123 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744727591 |
| source | Wiley-Blackwell Journals |
| subjects | asymmetric catalysis Asymmetry cascade reactions Cascades Catalysis Construction dicyanoalkenes Michael addition Michael reaction organocatalysis Stereoselectivity Synthesis |
| title | Asymmetric Vinylogous Michael Addition/Cyclization Cascade Reaction for the Construction of Diversely Structured Spiro- Oxindole Skeletons |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-17T15%3A42%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=Asymmetric%20Vinylogous%20Michael%20Addition/Cyclization%20Cascade%20Reaction%20for%20the%20Construction%20of%20Diversely%20Structured%20Spiro-%20Oxindole%20Skeletons&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Shi,%20Xiao-Mei&rft.date=2013-11-11&rft.volume=355&rft.issue=16&rft.spage=3119&rft.epage=3123&rft.pages=3119-3123&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201300329&rft_dat=%3Cproquest_cross%3E1494315575%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=1494315575&rft_id=info:pmid/&rfr_iscdi=true |