DABCO-Catalyzed α-Regio- and Diastereoselective (3+2) Cycloadditions of Nitrone Ylides from Isatins and Activated Alkenes

Abstract

α-Regio- and diastereoselective (3+2) cycloadditions of nitrone ylides derived from isatins with activated alkenes have been demonstrated. This mild protocol allows rapid access to a wide range of 3′,5′-diaryl-1′-hydroxy-2-oxospiro[indoline-3,2′-pyrrolidine] derivatives by using DABCO as an efficient catalyst. This method could also be carried out through three-component reaction efficiently in good yields and excellent diastereoselectivity.

Key words

nitrone ylide - cyclization - spirooxindole - regioselectivity - diastereoselectivity - isatin

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• 13 For details see the Supporting Information.
• 14 The structures of 3l and 3v were determined by single-crystal X-ray diffraction analyses. CCDC 1991838 for 3l and CCDC 2016378 for 3v contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. For details see also the Supporting Information.