A direct catalytic asymmetric vinylogous Mannich-type reaction has been disclosed in good yield, excellent regio-, diastereo- and enantioselectivity. The key to control the regioselectivity is the combination of a bulky N-acylpyrazole and a bulky bisphosphine ligand. The catalytic system was extended to a bisvinylogous Mannich-type reaction by changing the ligand. The synthetic utility of the vinylogous products was demonstrated by several transformations.

•3-CF3-oxindoles were obtained in good yield.•Asymmetric sulfenylation of 3-CF3-oxindole was obtained in 84% yield and with 94% ee.•The electro-donating groups of 3-CF3-oxindoles were well tolerated.•The electro-donating groups of sulfenylation reagents were well tolerated.•The electro-withdrawing groups of sulfenylation reagents were also well tolerated.An asymmetric sulfenylation of 3-CF3-oxindoles catalyzed by a quinidine derivative was described. 3-CF3-oxindoles with electro-donating groups led to corresponding products in good yield and with good enantioselectivity while 3-CF3-oxindoles bearing electro-withdrawing groups were not competent substrates due to its significant decomposition at the optimal reaction conditions. As for the sulfenylation reagents based on thiophenol, both electro-donating groups and electro-withdrawing groups were well tolerated.Download high-res image (101KB)Download full-size image