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dc.contributor.authorZhang, Jing
dc.contributor.authorAjitha, Manjaly John
dc.contributor.authorHe, Lin
dc.contributor.authorLiu, Kai
dc.contributor.authorDai, Bin
dc.contributor.authorHuang, Kuo-Wei
dc.date.accessioned2015-08-03T12:32:19Z
dc.date.available2015-08-03T12:32:19Z
dc.date.issued2015-03-13
dc.identifier.issn16154150
dc.identifier.doi10.1002/adsc.201400977
dc.identifier.urihttp://hdl.handle.net/10754/564104
dc.description.abstractThe first organocatalytic asymmetric synthesis of 4H-chromenes bearing a trifluoromethylated tetrasubstituted carbon center is presented. Chiral secondary amines promote the oxa-Michael-aldol cascade reaction between alkynals and 2-trifluoroacetylphenols via iminium-allenamine activation to produce pharmaceutically important heterocycles with excellent enantioselectivities. The proposed reaction can be scaled-up easily with maintenance of the excellent enantioselectivity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
dc.description.sponsorshipThis work was supported by the National Natural Science Foundation of China (Nos. 21162022, 21428302) and Shihezi University (Nos. 2011ZRKXTD04, 2012ZRKXJQ06).
dc.publisherWiley
dc.subject4H-chromenes
dc.subjectcascade reaction
dc.subjectiminium-allenamine activation
dc.subjectorganocatalysis
dc.subjecttrifluoromethylated tetrasubstituted carbon center
dc.titleEnantioselective organocatalyzed Oxa-Michael-Aldol cascade reactions: Construction of chiral 4H-chromenes with a trifluoromethylated tetrasubstituted carbon stereocenter
dc.typeArticle
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalAdvanced Synthesis & Catalysis
dc.contributor.institutionSchool of Chemistry and Chemical Engineering, Shihezi University, Xinjiang Uygur Autonomous Region, China
kaust.personHuang, Kuo-Wei
kaust.personAjitha, Manjaly John
dc.relation.issupplementedbyDOI:10.5517/cc13gxj0
display.relations<b> Is Supplemented By:</b> <br/> <ul><li><i>[Dataset]</i> <br/> Zhang, J., Ajitha, M. J., He, L., Liu, K., Dai, B., & Huang, K.-W. (2015). CCDC 1027232: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc13gxj0. DOI: <a href="https://doi.org/10.5517/cc13gxj0">10.5517/cc13gxj0</a> HANDLE: <a href="http://hdl.handle.net/10754/624375">10754/624375</a></li></ul>
dc.date.published-online2015-03-13
dc.date.published-print2015-03-23


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