Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst.
The current article reports an organocatalytic strategy for the asymmetric catalysis of chiral oxindoles bearing 3-position all-carbon quaternary stereocenters. Accordingly, highly enantioselective Michael addition reactions of 3-substituted oxindoles to terminal alkenes have been developed by utilizing a bifunctional tertiary-amine thiourea catalyst. The reactions accommodate a number of Michael donor compounds (different substituted 3-aryl or methyl oxindoles), and Michael acceptor compounds (vinyl ketones and vinyl sulfones) to give the desired oxindole products with moderate to excellent yields (up to 99%) and moderate to excellent enantioselectivities (up to 91% ee).
Li
Xin
X
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
Xi
Zhi-Guo
ZG
Luo
Sanzhong
S
Cheng
Jin-Pei
JP