Construction of tetrahydropyranoquinoline derivatives an asymmetric organocatalytic aza-Michael-IED/HAD cascade reaction
Chiral functionalized tetrahydroquinolines and pyranoquinolines with multiple stereogenic centres have emerged as attractive structures for derivatizing bioactive complex molecules. Herein, we develop a novel, facile organocatalytic asymmetric aza-Michael-IED/HAD cascade reaction of ( E )-ethyl 4-(2...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2017-11, Vol.15 (45), p.963-9637 |
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| container_issue | 45 |
| container_start_page | 963 |
| container_title | Organic & biomolecular chemistry |
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| creator | Dai, Lu Hou, Yuxuan Zhang, Lvye Chen, Zhangtao Zeng, Xiaofei Zhong, Guofu |
| description | Chiral functionalized tetrahydroquinolines and pyranoquinolines with multiple stereogenic centres have emerged as attractive structures for derivatizing bioactive complex molecules. Herein, we develop a novel, facile organocatalytic asymmetric aza-Michael-IED/HAD cascade reaction of (
E
)-ethyl 4-(2-(4-methylphenylsulfon amido)phenyl)-2-oxobut-3-enoate and enals. This method enables a convenient, powerful, and atom-economical access to various desired tetrahydropyranoquinoline derivatives with control of four stereogenic centres in good yields (up to 88%) with excellent diastereo- and enantioselectivities (up to >99 : 1 dr and >99% ee, respectively).
A highly efficient organocatalytic asymmetric aza-Michael-IED/HAD cascade reaction of (
E
)-ethyl 4-(2-(4-methylphenylsulfonamido)phenyl)-2-oxobut-3-enoate and enals is reported. |
| doi_str_mv | 10.1039/c7ob02231j |
| format | Article |
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E
)-ethyl 4-(2-(4-methylphenylsulfon amido)phenyl)-2-oxobut-3-enoate and enals. This method enables a convenient, powerful, and atom-economical access to various desired tetrahydropyranoquinoline derivatives with control of four stereogenic centres in good yields (up to 88%) with excellent diastereo- and enantioselectivities (up to >99 : 1 dr and >99% ee, respectively).
A highly efficient organocatalytic asymmetric aza-Michael-IED/HAD cascade reaction of (
E
)-ethyl 4-(2-(4-methylphenylsulfonamido)phenyl)-2-oxobut-3-enoate and enals is reported.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c7ob02231j</identifier><ispartof>Organic & biomolecular chemistry, 2017-11, Vol.15 (45), p.963-9637</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Dai, Lu</creatorcontrib><creatorcontrib>Hou, Yuxuan</creatorcontrib><creatorcontrib>Zhang, Lvye</creatorcontrib><creatorcontrib>Chen, Zhangtao</creatorcontrib><creatorcontrib>Zeng, Xiaofei</creatorcontrib><creatorcontrib>Zhong, Guofu</creatorcontrib><title>Construction of tetrahydropyranoquinoline derivatives an asymmetric organocatalytic aza-Michael-IED/HAD cascade reaction</title><title>Organic & biomolecular chemistry</title><description>Chiral functionalized tetrahydroquinolines and pyranoquinolines with multiple stereogenic centres have emerged as attractive structures for derivatizing bioactive complex molecules. Herein, we develop a novel, facile organocatalytic asymmetric aza-Michael-IED/HAD cascade reaction of (
E
)-ethyl 4-(2-(4-methylphenylsulfon amido)phenyl)-2-oxobut-3-enoate and enals. This method enables a convenient, powerful, and atom-economical access to various desired tetrahydropyranoquinoline derivatives with control of four stereogenic centres in good yields (up to 88%) with excellent diastereo- and enantioselectivities (up to >99 : 1 dr and >99% ee, respectively).
A highly efficient organocatalytic asymmetric aza-Michael-IED/HAD cascade reaction of (
E
)-ethyl 4-(2-(4-methylphenylsulfonamido)phenyl)-2-oxobut-3-enoate and enals is reported.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFjz0LwjAYhIMo-Lm4C_kD1aStlo7iBzq4uZfXNNpIm-ibKMZfbxHR0enuuAeOI2TI2ZizKJ2IxBxYGEb83CAdHidJwKZR2vz6kLVJ19ozYzxNZnGHPBZGW4c34ZTR1Bypkw6h8Dmai0fQ5npT2pRKS5pLVHdw6i4tBU3B-qqqYSWowVNNCnBQeldneEKwU6IAWQbb1XKymS-pACsglxQlvLf6pHWE0srBR3tktF7tF5sArcguqCpAn_3uRP_6F183UQ4</recordid><startdate>20171122</startdate><enddate>20171122</enddate><creator>Dai, Lu</creator><creator>Hou, Yuxuan</creator><creator>Zhang, Lvye</creator><creator>Chen, Zhangtao</creator><creator>Zeng, Xiaofei</creator><creator>Zhong, Guofu</creator><scope/></search><sort><creationdate>20171122</creationdate><title>Construction of tetrahydropyranoquinoline derivatives an asymmetric organocatalytic aza-Michael-IED/HAD cascade reaction</title><author>Dai, Lu ; Hou, Yuxuan ; Zhang, Lvye ; Chen, Zhangtao ; Zeng, Xiaofei ; Zhong, Guofu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c7ob02231j3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dai, Lu</creatorcontrib><creatorcontrib>Hou, Yuxuan</creatorcontrib><creatorcontrib>Zhang, Lvye</creatorcontrib><creatorcontrib>Chen, Zhangtao</creatorcontrib><creatorcontrib>Zeng, Xiaofei</creatorcontrib><creatorcontrib>Zhong, Guofu</creatorcontrib><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dai, Lu</au><au>Hou, Yuxuan</au><au>Zhang, Lvye</au><au>Chen, Zhangtao</au><au>Zeng, Xiaofei</au><au>Zhong, Guofu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Construction of tetrahydropyranoquinoline derivatives an asymmetric organocatalytic aza-Michael-IED/HAD cascade reaction</atitle><jtitle>Organic & biomolecular chemistry</jtitle><date>2017-11-22</date><risdate>2017</risdate><volume>15</volume><issue>45</issue><spage>963</spage><epage>9637</epage><pages>963-9637</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Chiral functionalized tetrahydroquinolines and pyranoquinolines with multiple stereogenic centres have emerged as attractive structures for derivatizing bioactive complex molecules. Herein, we develop a novel, facile organocatalytic asymmetric aza-Michael-IED/HAD cascade reaction of (
E
)-ethyl 4-(2-(4-methylphenylsulfon amido)phenyl)-2-oxobut-3-enoate and enals. This method enables a convenient, powerful, and atom-economical access to various desired tetrahydropyranoquinoline derivatives with control of four stereogenic centres in good yields (up to 88%) with excellent diastereo- and enantioselectivities (up to >99 : 1 dr and >99% ee, respectively).
A highly efficient organocatalytic asymmetric aza-Michael-IED/HAD cascade reaction of (
E
)-ethyl 4-(2-(4-methylphenylsulfonamido)phenyl)-2-oxobut-3-enoate and enals is reported.</abstract><doi>10.1039/c7ob02231j</doi><tpages>8</tpages></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2017-11, Vol.15 (45), p.963-9637 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Construction of tetrahydropyranoquinoline derivatives an asymmetric organocatalytic aza-Michael-IED/HAD cascade reaction |
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