title: Asymmetric Michael reaction of aldehydes with β-nitroalkenes catalyzed by pyrrolidine-camphor derived organocatalysts bearing hydrogen-bond donors.
abstract: Several pyrrolidine-camphor derived organocatalysts were designed and synthesized. These organocatalysts were used for direct Michael reaction of aldehydes with nitroalkenes to give the desired γ-nitrocarbonyl compounds in high yields (up to 99%), high diastereoselectivities (syn:anti up to 92:8), and good to excellent enantioselectivities (up to 94% ee). Possible transition-state model was also proposed for this asymmetric transformation, which may involve hydrogen-bond interactions between the nucleophilic enamine formed in situ and the nitroalkenes.
authors.affiliation: Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, People's Republic of China.
authors.forename: Jiang
authors.initials: J
authors.lastname: Weng
authors.forename: Hui-Bing
authors.initials: HB
authors.lastname: Ai
authors.forename: Ren-Shi
authors.initials: RS
authors.lastname: Luo
authors.forename: Gui
authors.initials: G
authors.lastname: Lu
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002164:Camphor / Q000737:chemistry*; D002384:Catalysis; D006860:Hydrogen Bonding; D008956:Models, Chemical; D011392:Proline / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000475:Alkenes; D011759:Pyrrolidines; D002164:Camphor; D011392:Proline; C032519:pyrrolidine