Bifunctional Thiourea–Ammonium Salt Catalysts Derived from Cinchona Alkaloids: Cooperative Phase-Transfer Catalysts in the Enantioselective Aza-Henry Reaction of Ketimines

An efficient enantioselective aza-Henry reaction of aryl α-ketoester-derived ketimines has been realized by using bifunctional thiourea–ammonium salt phase-transfer catalysts, which were derived from quinine. A variety of aryl α-ketoester-derived N-Ts ketimines were investigated, and the correspondi...

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Veröffentlicht in:	Journal of organic chemistry 2018-02, Vol.83 (3), p.1486-1492
Hauptverfasser:	Lu, Ning, Fang, Yanhong, Gao, Yuan, Wei, Zhonglin, Cao, Jungang, Liang, Dapeng, Lin, Yingjie, Duan, Haifeng
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Sprache:	eng
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container_end_page	1492
container_issue	3
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container_title	Journal of organic chemistry
container_volume	83
creator	Lu, Ning Fang, Yanhong Gao, Yuan Wei, Zhonglin Cao, Jungang Liang, Dapeng Lin, Yingjie Duan, Haifeng
description	An efficient enantioselective aza-Henry reaction of aryl α-ketoester-derived ketimines has been realized by using bifunctional thiourea–ammonium salt phase-transfer catalysts, which were derived from quinine. A variety of aryl α-ketoester-derived N-Ts ketimines were investigated, and the corresponding products were obtained in high to excellent yields (up to 99%) with good to high enantioselectivities (up to >99% ee).
doi_str_mv	10.1021/acs.joc.7b03078
format	Article
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Org. Chem</addtitle><date>2018-02-02</date><risdate>2018</risdate><volume>83</volume><issue>3</issue><spage>1486</spage><epage>1492</epage><pages>1486-1492</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>An efficient enantioselective aza-Henry reaction of aryl α-ketoester-derived ketimines has been realized by using bifunctional thiourea–ammonium salt phase-transfer catalysts, which were derived from quinine. A variety of aryl α-ketoester-derived N-Ts ketimines were investigated, and the corresponding products were obtained in high to excellent yields (up to 99%) with good to high enantioselectivities (up to >99% ee).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>29271656</pmid><doi>10.1021/acs.joc.7b03078</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-1424-5714</orcidid></addata></record>
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title	Bifunctional Thiourea–Ammonium Salt Catalysts Derived from Cinchona Alkaloids: Cooperative Phase-Transfer Catalysts in the Enantioselective Aza-Henry Reaction of Ketimines
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