title: Stereoselective synthesis of 1,3-amino alcohols by the Pd-catalyzed cyclization of trichloroacetimidates.
abstract: The synthesis of 4-vinyl-5,6-dihydro-1,3-oxazines, precursors of 1,3-amino alcohols, using the palladium-catalyzed cyclization of trichloroacetimidates is reported. The reaction favors the formation of the 4,6-cis-isomers with up to >20:1 diastereoselectivity. Chemoselective hydrolysis of the resulting 5,6-dihydro-1,3-oxazines was also investigated.
authors.forename: Yuanzhen
authors.initials: Y
authors.lastname: Xie
authors.forename: Kai
authors.initials: K
authors.lastname: Yu
authors.forename: Zhenhua
authors.initials: Z
authors.lastname: Gu
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D062845:Chloroacetates / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000081:Acetamides; D000605:Amino Alcohols; D062845:Chloroacetates; D010078:Oxazines; D010165:Palladium; C009528:trichloroacetamide