title: Highly enantioselective Michael addition promoted by a new diterpene-derived bifunctional thiourea catalyst: a doubly stereocontrolled approach to chiral succinimide derivatives.
abstract: A doubly stereocontrolled organocatalytic asymmetric Michael addition to the synthesis of substituted succinimides is described. Starting from aldehydes and maleimides, both enantiomers of the succinimides could be obtained in high to excellent yields (up to 98%) and enantioselectivities (up to 99%) when one of the two special chiral diterpene-derived bifunctional thioureas was individually used as a catalyst. Moreover, these catalysts can be efficiently used in large-scale catalytic synthesis with the same level of yield and enantioselectivity.
authors.affiliation: College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan, People's Republic of China.
authors.forename: Zhong-Tai
authors.initials: ZT
authors.lastname: Song
authors.forename: Tao
authors.initials: T
authors.lastname: Zhang
authors.forename: Hai-Long
authors.initials: HL
authors.lastname: Du
authors.forename: Zhi-Wei
authors.initials: ZW
authors.lastname: Ma
authors.forename: Chang-Hua
authors.initials: CH
authors.lastname: Zhang
authors.forename: Jing-Chao
authors.initials: JC
authors.lastname: Tao
mesh_terms: D002384:Catalysis; D004224:Diterpenes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
chemical_list: D004224:Diterpenes; D013388:Succinimides; C032620:succinimide; D013890:Thiourea
keywords: Michael reaction; diterpene-derived thiourea; enantiomers; maleimide; succinimide