Asymmetric synthesis of 4H-1,3-oxazines: enantioselective reductive cyclization of N-acylated beta-amino enones with trichlorosilane catalyzed by chiral Lewis bases.
N-Acylated beta-amino enones reductively cyclize by treatment with trichlorosilane and a chiral Lewis base catalyst to afford optically active 4H-1,3-oxazines, which can be transformed to other chiral compounds without racemization.
Sugiura
Masaharu
M
Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan. msugiura@kumamoto-u.ac.jp
Kumahara
Mako
M
Nakajima
Makoto
M
D000107:Acetylation; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D010078:Oxazines; D012821:Silanes; C065893:trichlorosilane