Organocatalytic asymmetric [3+2] cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with 3-alkenyl-5-arylfuran-2(3H)-onesElectronic supplementary information (ESI) available: Experimental procedures, spectral data of new compounds, and crystallographic data. CCDC 1474514. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6cc06367e

A highly diastereo- and enantioselective [3+2] cycloaddition reaction of N -2,2,2-trifluoroethylisatin ketimines and 3-alkenyl-5-arylfuran-2(3 H )-ones was developed with 1 mol% thiourea-tertiary amine as the catalyst. A series of spiro[pyrrolidin-3,2′-oxindoles] bearing four consecutive stereocente...

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Main Authors Wang, Zhen-Hua, Wu, Zhi-Jun, Yue, Deng-Feng, Hu, Wen-Fei, Zhang, Xiao-Mei, Xu, Xiao-Ying, Yuan, Wei-Cheng
Format Journal Article
Published 22.09.2016
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Summary:A highly diastereo- and enantioselective [3+2] cycloaddition reaction of N -2,2,2-trifluoroethylisatin ketimines and 3-alkenyl-5-arylfuran-2(3 H )-ones was developed with 1 mol% thiourea-tertiary amine as the catalyst. A series of spiro[pyrrolidin-3,2′-oxindoles] bearing four consecutive stereocenters, including two vicinal spiro-quaternary chiral centers, were efficiently obtained with excellent results (up to >99% yield, >20 : 1 dr, and >99% ee). An asymmetric [3+2] cycloaddition reaction of N -2,2,2-trifluoroethylisatin ketimines and 3-alkenyl-5-arylfuran-2(3 H )-ones was developed with 1 mol% thiourea-tertiary amine.
Bibliography:For ESI and crystallographic data in CIF or other electronic format see DOI
1474514
Electronic supplementary information (ESI) available: Experimental procedures, spectral data of new compounds, and crystallographic data. CCDC
10.1039/c6cc06367e
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc06367e