title: Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition.
abstract: A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er). These reactions were enabled by a quinine-derived primary-tertiary diamine as a catalyst and pentafluoropropionic acid (PFP) as a co-catalyst.
authors.affiliation: State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, 22 Hankou Road, Nanjing 210093, China. yushouyun@nju.edu.cn.
authors.forename: Shuanghua
authors.initials: S
authors.lastname: Cheng
authors.forename: Shouyun
authors.initials: S
authors.lastname: Yu
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D005466:Fluorocarbons / Q000737:chemistry*; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis*; D011803:Quinine / Q000031:analogs & derivatives*; D013237:Stereoisomerism
chemical_list: D005466:Fluorocarbons; D010078:Oxazines; C033093:perfluoropropionic acid; D011803:Quinine