Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N -Boc ketimines catalyzed by chiral phase-transfer catalysts
A highly diastereo- and enantioselective nitro-Mannich reaction of isatin-derived ketimines with α-aryl nitromethane catalyzed by Cinchona alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed....
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| Veröffentlicht in: | New journal of chemistry 2018, Vol.42 (3), p.1608-1611 |
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| container_issue | 3 |
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| container_title | New journal of chemistry |
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| creator | Liu, Yuxin Wang, Jingdong Wei, Zhonglin Cao, Jungang Liang, Dapeng Lin, Yingjie Duan, Haifeng |
| description | A highly diastereo- and enantioselective nitro-Mannich reaction of isatin-derived ketimines with α-aryl nitromethane catalyzed by
Cinchona
alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed. A series of 3-substituted 3-amino-oxindoles were constructed using this protocol in excellent yields (96–99%) with high enantioselectivities (up to 95% ee) and diastereoselectivities (up to 95 : 5 dr). |
| doi_str_mv | 10.1039/C7NJ04527A |
| format | Article |
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Cinchona
alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed. A series of 3-substituted 3-amino-oxindoles were constructed using this protocol in excellent yields (96–99%) with high enantioselectivities (up to 95% ee) and diastereoselectivities (up to 95 : 5 dr).</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/C7NJ04527A</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Catalysis ; Hydrogen bonding ; Imines ; Nitromethane ; Phase transfer catalysts</subject><ispartof>New journal of chemistry, 2018, Vol.42 (3), p.1608-1611</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c325t-6e6a50384e488a2b8f2bc9dd2fa5e4bf75ebbbcf8c4f8a09f2d5db19ee3e803c3</citedby><cites>FETCH-LOGICAL-c325t-6e6a50384e488a2b8f2bc9dd2fa5e4bf75ebbbcf8c4f8a09f2d5db19ee3e803c3</cites><orcidid>0000-0001-7410-6092 ; 0000-0001-8492-6609</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4010,27900,27901,27902</link.rule.ids></links><search><creatorcontrib>Liu, Yuxin</creatorcontrib><creatorcontrib>Wang, Jingdong</creatorcontrib><creatorcontrib>Wei, Zhonglin</creatorcontrib><creatorcontrib>Cao, Jungang</creatorcontrib><creatorcontrib>Liang, Dapeng</creatorcontrib><creatorcontrib>Lin, Yingjie</creatorcontrib><creatorcontrib>Duan, Haifeng</creatorcontrib><title>Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N -Boc ketimines catalyzed by chiral phase-transfer catalysts</title><title>New journal of chemistry</title><description>A highly diastereo- and enantioselective nitro-Mannich reaction of isatin-derived ketimines with α-aryl nitromethane catalyzed by
Cinchona
alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed. A series of 3-substituted 3-amino-oxindoles were constructed using this protocol in excellent yields (96–99%) with high enantioselectivities (up to 95% ee) and diastereoselectivities (up to 95 : 5 dr).</description><subject>Aromatic compounds</subject><subject>Catalysis</subject><subject>Hydrogen bonding</subject><subject>Imines</subject><subject>Nitromethane</subject><subject>Phase transfer catalysts</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpFkEtLAzEUhYMoWKsbf0HAnRDNY57LWt_UutH1cCdzQ1OnSU1Sof4Af7cjLbg6l3M-zoVDyLngV4Kr-npazp95lstyckBGQhU1q2UhDodbZBnjeVYck5MYl5wLURZiRH5uLcSEAT2j4DqKDlyyPmKPOtkvpM6m4NkLOGf1ggaEwfaOekNthGQd6zAMXEfnlN14TT8w2ZV1GKmGBP32e4jaLdULG6Cn6wVEZCmAiwbDHokpnpIjA33Es72Oyfv93dv0kc1eH56mkxnTSuaJFVhAzlWVYVZVINvKyFbXXScN5Ji1psyxbVttKp2ZCnhtZJd3ragRFVZcaTUmF7vedfCfG4ypWfpNcMPLRnLBq1LxoX9MLneUDj7GgKZZB7uCsG0Eb_52bv53Vr83anNl</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Liu, Yuxin</creator><creator>Wang, Jingdong</creator><creator>Wei, Zhonglin</creator><creator>Cao, Jungang</creator><creator>Liang, Dapeng</creator><creator>Lin, Yingjie</creator><creator>Duan, Haifeng</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0001-7410-6092</orcidid><orcidid>https://orcid.org/0000-0001-8492-6609</orcidid></search><sort><creationdate>2018</creationdate><title>Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N -Boc ketimines catalyzed by chiral phase-transfer catalysts</title><author>Liu, Yuxin ; Wang, Jingdong ; Wei, Zhonglin ; Cao, Jungang ; Liang, Dapeng ; Lin, Yingjie ; Duan, Haifeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-6e6a50384e488a2b8f2bc9dd2fa5e4bf75ebbbcf8c4f8a09f2d5db19ee3e803c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aromatic compounds</topic><topic>Catalysis</topic><topic>Hydrogen bonding</topic><topic>Imines</topic><topic>Nitromethane</topic><topic>Phase transfer catalysts</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Yuxin</creatorcontrib><creatorcontrib>Wang, Jingdong</creatorcontrib><creatorcontrib>Wei, Zhonglin</creatorcontrib><creatorcontrib>Cao, Jungang</creatorcontrib><creatorcontrib>Liang, Dapeng</creatorcontrib><creatorcontrib>Lin, Yingjie</creatorcontrib><creatorcontrib>Duan, Haifeng</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Yuxin</au><au>Wang, Jingdong</au><au>Wei, Zhonglin</au><au>Cao, Jungang</au><au>Liang, Dapeng</au><au>Lin, Yingjie</au><au>Duan, Haifeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N -Boc ketimines catalyzed by chiral phase-transfer catalysts</atitle><jtitle>New journal of chemistry</jtitle><date>2018</date><risdate>2018</risdate><volume>42</volume><issue>3</issue><spage>1608</spage><epage>1611</epage><pages>1608-1611</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>A highly diastereo- and enantioselective nitro-Mannich reaction of isatin-derived ketimines with α-aryl nitromethane catalyzed by
Cinchona
alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed. A series of 3-substituted 3-amino-oxindoles were constructed using this protocol in excellent yields (96–99%) with high enantioselectivities (up to 95% ee) and diastereoselectivities (up to 95 : 5 dr).</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C7NJ04527A</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-7410-6092</orcidid><orcidid>https://orcid.org/0000-0001-8492-6609</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2018, Vol.42 (3), p.1608-1611 |
| issn | 1144-0546 1369-9261 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aromatic compounds Catalysis Hydrogen bonding Imines Nitromethane Phase transfer catalysts |
| title | Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N -Boc ketimines catalyzed by chiral phase-transfer catalysts |
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