title: Dual-organocatalyst-promoted asymmetric cascade reaction: highly efficient construction of enantiopure fully substituted tetrahydro-1,2-oxazines.
abstract: A four-component asymmetric α-aminoxylation/aza-Michael/Mannich cascade reaction for the construction of fully substituted chiral tetrahydro-1,2-oxazine derivatives was accomplished in high yields with excellent enantio- and diastereoselectivities under mild conditions. The 1,2-oxazine derivative could be transformed to the corresponding multifunctional chiral amino alcohol by N-O cleavage and fused-tricyclic 4-amino-substituted tetrahydroquinolines in good yields with excellent stereoselectivities followed by a Friedel-Crafts reaction. Also a 4-alkoxy-substituted tetrahydroquinoline was achieved by C-4 inversion of a 4-amino-substituted tetrahydroquinoline.
authors.affiliation: Department of Chemistry, Fudan University , 220 Handan Road, Shanghai, 200433, P. R. China.
authors.forename: Hua
authors.initials: H
authors.lastname: Lin
authors.forename: Xing-Wen
authors.initials: XW
authors.lastname: Sun
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D011083:Polycyclic Compounds / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D010078:Oxazines; D011083:Polycyclic Compounds; D011804:Quinolines