DABCO-promoted highly diastereo- and regioselective construction of C-3 functionalized spirooxindoles via [3 + 2] cycloaddition of 2-aryl/heteroarylidene-1H-indene-1,3(2H)-diones with N-2,2,2-trifluoroethylisatin ketimines at ambient conditions?

RSC Advances Pub Date: 2022-12-06 DOI: 10.1039/D2RA07141J

Abstract

The application of 2-aryl/heteroarylidene-1H-indene-1,3(2H)-dione as an activated olefin source in the DABCO-catalyzed [3 + 2] cycloaddition with N-2,2,2-trifluoroethylisatin ketimines has been disclosed. This highly efficient 1,3-dipolar cycloaddition reaction offered a variety of trifluoro methyl group bearing spiro-pyrrolidine linked oxindoles with four consecutive stereocentres in good to excellent yield and excellent diastereoselectivity. The synthetic practicality of the protocol was established by demonstrating the enantioselective construction of spiro-pyrrolidine-oxindoles with two vicinal spiro-quaternary chiral centres in good yield excellent enantioselectivity (>90% ee) by using ultralow loading of quinine as the catalyst at room temperature.

Graphical abstract: DABCO-promoted highly diastereo- and regioselective construction of C-3 functionalized spirooxindoles via [3 + 2] cycloaddition of 2-aryl/heteroarylidene-1H-indene-1,3(2H)-diones with N-2,2,2-trifluoroethylisatin ketimines at ambient conditions
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