title: A new synthetic route for axially chiral secondary amines with binaphthyl backbone and their applications in asymmetric Michael reaction of aldehydes to nitroalkenes.
abstract: A new synthetic route for binaphthyl-based secondary amines has been developed. The key features of this route include the selective direct esterification of the binaphthyl structure at the 3- or 3,3'-position and the methylation by a Negishi cross-coupling reaction. Based on the new approach, a series of 3-monosubstituted and 3,3'-disubstituted chiral secondary amines with a binaphthyl backbone were synthesized and screened in the Michael reaction of aldehydes to various nitroalkenes. 3-Monosubstituted secondary amine 7c was proved to be the best catalyst, affording high yields (up to 95%), good to excellent enantioselectivities (up to 99%) and diastereoselectivities (syn/anti up to 99:1) under the optimized conditions.
authors.affiliation: Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
authors.forename: Da-Cheng
authors.initials: DC
authors.lastname: Liang
authors.forename: Ren-Shi
authors.initials: RS
authors.lastname: Luo
authors.forename: Li-Hua
authors.initials: LH
authors.lastname: Yin
authors.forename: Albert S C
authors.initials: AS
authors.lastname: Chan
authors.forename: Gui
authors.initials: G
authors.lastname: Lu
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis*; D002384:Catalysis; D004951:Esterification; D008745:Methylation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000588:Amines; D009281:Naphthalenes; D009574:Nitro Compounds