Enantioselective organocatalyzed Oxa-Michael-Aldol cascade reactions: Construction of chiral 4H-chromenes with a trifluoromethylated tetrasubstituted carbon stereocenter
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2015-03-13
Print Publication Date2015-03-23
Permanent link to this recordhttp://hdl.handle.net/10754/564104
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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.
CitationZhang, J., Ajitha, M. J., He, L., Liu, K., Dai, B., & Huang, K.-W. (2015). Enantioselective Organocatalyzed Oxa-Michael-Aldol Cascade Reactions: Construction of Chiral 4H-Chromenes with a Trifluoromethylated Tetrasubstituted Carbon Stereocenter. Advanced Synthesis & Catalysis, 357(5), 967–973. doi:10.1002/adsc.201400977
SponsorsThis work was supported by the National Natural Science Foundation of China (Nos. 21162022, 21428302) and Shihezi University (Nos. 2011ZRKXTD04, 2012ZRKXJQ06).
JournalAdvanced Synthesis & Catalysis
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