Highly diastereo- and enantioselective Michael additions of 3-substituted oxindoles to maleimides catalyzed by chiral bifunctional thiourea-tertiary amine.
A highly diastereo- and enantioselective Michael addition reaction with respect to prochiral 3-substituted oxindoles and maleimides by a chiral bifunctional thiourea-tertiary amine catalyst was investigated for the first time. The corresponding adducts, containing a quaternary center at the C3-position of the oxindole as well as a vicinal tertiary center, were generally obtained in good to high yields (up to 92%) with high to excellent diastereo- (up to 99:1 dr) and enantioselectivities (up to 99% ee).
Liao
Yu-Hua
YH
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Liu
Xiong-Li
XL
Wu
Zhi-Jun
ZJ
Cun
Lin-Feng
LF
Zhang
Xiao-Mei
XM
Yuan
Wei-Cheng
WC
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000588:Amines; D007211:Indoles; D008301:Maleimides; D000078183:Oxindoles; C022960:2-oxindole; D013890:Thiourea