A new strategy for the construction of optically active 5'-CF3 spiro[pyrrolidin-3,2'-oxindole] was described. A series of unprecedented 1,3-dipoles were obtained by condensation of CF3CH2NH2 with isatins. The 1,3-dipolar cycloaddition reactions of these ketimines with enals gave the products bearing four contiguous stereogenic centers in excellent yields, diastereoselectivities and enantioselectivities.

The first asymmetric aza-Friedel-Crafts reaction of indoles and pyrroles with isatin-derived N-Boc ketimines catalyzed by chiral phosphoric acids is reported. In general, derivatives of substituted 3-amino-2-oxindoles were obtained with excellent enantioselectivities and high yields.

A Cinchona alkaloid-derived squaramidecatalyzed asymmetric cycloaddition of trfluoromethyl-containing azomethine ylides with b-nitroalkenes was realized under mild conditions.Aserieso fb iologically important 5'-trifluoromethyl-spiro[pyrrolidin-3,2'-oxindoles] was synthesizede fficiently by this process in excellent yields,e nantioseletivities and diastereoselectivities.

A catalytic asymmetric method for the synthesis of 2-CF3 chromanes has been described. Generally, the squaramide-catalyzed cascade reaction of 2-hydroxychalcones with β-CF3-nitroalkenes gave the CF3-containing heterocyclic compounds bearing three contiguous stereogenic centers in excellent yields, diastereoselectivities, and enantioselectivities.