Organocatalytic asymmetric Michael addition of α-alkylidene succinimides to nitrostyrenes.
A bifunctional squaramide-catalyzed asymmetric Michael addition reaction of α-alkylidene succinimides with nitrostyrenes and a nitrodiene has been developed. This organocatalytic asymmetric reaction provides easy access to functionalized succinimides with two contiguous stereocenters with a broad substrate scope. The desired succinimide derivatives were obtained in good to excellent yields (up to 98%) with high to excellent diastereoselectivities (up to >99 : 1 dr) and excellent enantioselectivities (up to 99% ee). This protocol provides a straightforward entry to functionalized chiral succinimide derivatives from simple starting materials.
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China. dudm@bit.edu.cn.
Bo-Liang
BL
Zhao
Dongxiang
D
Zhang
Lei
L
Liu
Da-Ming
DM
Du
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D008968:Molecular Conformation; D011803:Quinine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry*
D000475:Alkenes; D013343:Styrenes; D013388:Succinimides; C000609819:squaramide; C011955:beta-nitrostyrene; D011803:Quinine