The spiroindoline unit is a privileged heterocyclic substructure in a widespread series of natural products and biologically active compounds. Isocyanides are versatile precursors that are used widely in cascade reactions to synthesis of heterocyclic compounds. 2-Isocyanoethylindole bearing a pendant nucleophilic isocyanide at the C3 position of indole serves as a readily available starting material to hold a particular high promise for spiroindolines with multiple stereocenters A highly efficient asymmetric dearomatization of indoles was realized via cascade 2-isocyanoethylindole to between alkylidene malonates and 3-alkenyl-oxindoles catalyzed by a chiral N,N′-dioxide–Mg(II) complex catalyst. Fused polycyclic indolines and spiroindolines containing multiple stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities via a Michael/Friedel–Crafts type cascade. References [a] X. H. Liu, L. L. Lin, X. M. Feng, Acc. Chem. Res. 2011, 44, 574-587 X. H. Liu, L. L. Lin, X. M. Feng, Org. Chem. Front. 2014, 1, 298-302. [c] X. H. Zhao, X. H. Liu, H. J. Mei, J. Guo, L. L. Lin, X. M. Feng, Angew. Chem. Int. Ed. 2015, 54, 4032-4035. [d] X. H. Zhao, X. H. Liu, Q. Xiong, H. J. Mei, B. W. Ma, L. L. Lin, X. M. Feng, Chem. Commun. DOI: 10.1039/C5CC06353A

Asymmetric dearomatization of indoles through Michael/Friedel-Crafts-type cascade to construct polycyclic spiroindolines

251st National Meeting (2016)

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