title: Chiral guanidine-catalyzed asymmetric direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactams with alkylidene malonates.
abstract: The asymmetric direct vinylogous Michael reaction of α,β-unsaturated γ-butyrolactams with alkylidene malonates has been developed. Various 5-substituted 3-pyrrolidin-2-ones were obtained in high yields (up to 93%) with excellent stereoselectivities (up to 94% ee, 95 : 5 dr), using a novel bifunctional C(1)-symmetric guanidine organocatalyst embodied a secondary amine subunit.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.forename: Shunxi
authors.initials: S
authors.lastname: Dong
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D019791:Guanidine / Q000138:chemical synthesis / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry*; D008314:Malonates / Q000138:chemical synthesis / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D008314:Malonates; D011760:Pyrrolidinones; D019791:Guanidine