title: High diastereoselective vinylogous Mannich reaction induced by O-pivaloylated D-galactosylamine as the chiral auxiliary: stereoselective synthesis of 8-arylazocan-2-one.
abstract: The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-amino aldehyde derivatives has been achieved with high yield via a vinylogous Mannich reaction. The reaction was performed by using a O-pivaloylated galactosyl amine as a chiral template and AlCl3 as a promoter in THF. (S)-8-(p-Nitrophenyl) azocan-2-one can be stereoselective synthesized from (S) ethyl 7-galactosylamino-7-(p-nitrophenyl)hepta-2,4-dienoate by sequential hydrogenation of the double bond, cyclic lactam formation, and removal of the N-glycosidic auxiliary under basic conditions.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors.forename: Bing
authors.initials: B
authors.lastname: Cui
authors.forename: Gang
authors.initials: G
authors.lastname: Hou
authors.forename: Yan
authors.initials: Y
authors.lastname: Cai
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Miao
mesh_terms: D005688:Galactosamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D005688:Galactosamine