Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One‐pot Three‐component Sequential Cascade Reactions
A bifunctional squaramide‐catalyzed one‐pot three‐component Michael/Mannich‐Michael/cyclization sequential cascade reaction for the construction of bispirooxindole‐spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamo...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2019-07, Vol.361 (14), p.3412-3419 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Zhao, Bo‐Liang Du, Da‐Ming |
| description | A bifunctional squaramide‐catalyzed one‐pot three‐component Michael/Mannich‐Michael/cyclization sequential cascade reaction for the construction of bispirooxindole‐spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamoyl‐3‐ylideneoxindoles have been applied to this sequential cascade strategy for the first time. This new strategy provides a process for the enantioselective construction of bispirooxindole‐spirooxindoles with seven stereocenters, of which three are quaternary spiro‐stereocenters. |
| doi_str_mv | 10.1002/adsc.201900218 |
| format | Article |
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A series of original cinnamoyl‐3‐ylideneoxindoles have been applied to this sequential cascade strategy for the first time. This new strategy provides a process for the enantioselective construction of bispirooxindole‐spirooxindoles with seven stereocenters, of which three are quaternary spiro‐stereocenters.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201900218</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Cascade chemical reactions ; Cascade reaction ; Chemical reactions ; Enantiomers ; Michael/cyclization ; Michael/Mannich ; Organocatalysis ; Spirooxindoles</subject><ispartof>Advanced synthesis & catalysis, 2019-07, Vol.361 (14), p.3412-3419</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. 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A series of original cinnamoyl‐3‐ylideneoxindoles have been applied to this sequential cascade strategy for the first time. This new strategy provides a process for the enantioselective construction of bispirooxindole‐spirooxindoles with seven stereocenters, of which three are quaternary spiro‐stereocenters.</description><subject>Cascade chemical reactions</subject><subject>Cascade reaction</subject><subject>Chemical reactions</subject><subject>Enantiomers</subject><subject>Michael/cyclization</subject><subject>Michael/Mannich</subject><subject>Organocatalysis</subject><subject>Spirooxindoles</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFULtOwzAUjRBIlMLKbIm5xU6c11iFp1SpEilz5NrX1FViBzttCRMfwMA38iW4Kioj0zlXOo-rEwSXBI8JxuE1E46PQ0xyf5DsKBiQhMQjSpL8-MBjfBqcObfCmKRZmg6Cz4nrmwY6qzgqe90twSmHjERlq6wxb0oLU4NDW9UtUQkb0KjswILhoD06tFEMzewL04azjtX9Owg00_D98dWaDs2XFnacm6Y12lt8xuvao2I1KpjjTAB6AsY7ZbQ7D04kqx1c_OIweL67nRcPo-ns_rGYTEc8imk2SoFGnDLB4ijHSSrDkIqccE4TITIeLRJBU5kuuJAsTiD1FQLnccgyzDMuhYyGwdU-t7XGf-O6amXWVvvKKgzjjISYksirxnsVt8Y5C7JqrWqY7SuCq93i1W7x6rC4N-R7w1bV0P-jriY3ZfHn_QG2CIuq</recordid><startdate>20190711</startdate><enddate>20190711</enddate><creator>Zhao, Bo‐Liang</creator><creator>Du, Da‐Ming</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20190711</creationdate><title>Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One‐pot Three‐component Sequential Cascade Reactions</title><author>Zhao, Bo‐Liang ; Du, Da‐Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3548-7e43c4ada539067f224d91cc46dd8c3b6d47f7bcdfa56e7aded0952a80c8cfdf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Cascade chemical reactions</topic><topic>Cascade reaction</topic><topic>Chemical reactions</topic><topic>Enantiomers</topic><topic>Michael/cyclization</topic><topic>Michael/Mannich</topic><topic>Organocatalysis</topic><topic>Spirooxindoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhao, Bo‐Liang</creatorcontrib><creatorcontrib>Du, Da‐Ming</creatorcontrib><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>Zhao, Bo‐Liang</au><au>Du, Da‐Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One‐pot Three‐component Sequential Cascade Reactions</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2019-07-11</date><risdate>2019</risdate><volume>361</volume><issue>14</issue><spage>3412</spage><epage>3419</epage><pages>3412-3419</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A bifunctional squaramide‐catalyzed one‐pot three‐component Michael/Mannich‐Michael/cyclization sequential cascade reaction for the construction of bispirooxindole‐spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamoyl‐3‐ylideneoxindoles have been applied to this sequential cascade strategy for the first time. This new strategy provides a process for the enantioselective construction of bispirooxindole‐spirooxindoles with seven stereocenters, of which three are quaternary spiro‐stereocenters.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201900218</doi><tpages>8</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Cascade chemical reactions Cascade reaction Chemical reactions Enantiomers Michael/cyclization Michael/Mannich Organocatalysis Spirooxindoles |
| title | Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One‐pot Three‐component Sequential Cascade Reactions |
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