title: Enantioselective synthesis of 3,4-dihydropyran derivatives via organocatalytic Michael reaction of α,β-unsaturated enones.
abstract: A simple chiral diamine catalyst (1a) was successfully applied in the asymmetric Michael reaction between cyclic dimedone and α,β-unsaturated ketones. Both acyclic enones with aryl or alkyl β-substituents and cyclic enones were tolerated well in the reaction. The desired adducts were obtained in high yields (up to 98%) with excellent enantioselectivities (up to 97% ee). The additives were found to increase the reactivity dramatically. The biologically active 2,4-disubstituted polyhydroquinoline scaffold was conveniently prepared through an ammoniation from the generated 3,4-dihydropyran product.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
authors.forename: Yangbin
authors.initials: Y
authors.lastname: Liu
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Min
authors.initials: M
authors.lastname: Wang
authors.forename: Peng
authors.initials: P
authors.lastname: He
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D002384:Catalysis; D003959:Diamines / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003959:Diamines; D007659:Ketones; D011714:Pyrans; C073813:3,4-dihydropyran