title: Enantioselective conjugate addition of both aromatic ketones and acetone to nitroolefins catalyzed by chiral primary amines bearing multiple hydrogen-bonding donors.
abstract: A new class of chiral primary amine catalysts bearing multiple hydrogen-bonding donors have been designed and synthesized. The newly developed bifunctional organocatalysts efficiently catalyzed not only enantioselective conjugate addition of aromatic ketones to nitroolefins in good yields (up to 87%) with excellent enantioselectivities (97→99% ee) but also enantioselective conjugate addition of acetone to nitroolefins in excellent yields (90-96%) with high enantioselectivities (up to 97% ee).
authors.affiliation: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
authors.forename: Zhong-Wen
authors.initials: ZW
authors.lastname: Sun
authors.forename: Fang-Zhi
authors.initials: FZ
authors.lastname: Peng
authors.forename: Ze-Qian
authors.initials: ZQ
authors.lastname: Li
authors.forename: Li-Wei
authors.initials: LW
authors.lastname: Zou
authors.forename: Shao-Xiong
authors.initials: SX
authors.lastname: Zhang
authors.forename: Xiang
authors.initials: X
authors.lastname: Li
authors.forename: Zhi-Hui
authors.initials: ZH
authors.lastname: Shao
mesh_terms: D000096:Acetone / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000588:Amines; D007659:Ketones; D000096:Acetone