Catalytic enantioselective synthesis of 4-vinyl-2-trichloromethyloxazoline: an access to enantioenriched vinylglycinol surrogate.
Cationic Pd(II) catalysts generated from chiral biphenyl diphosphine complexes or from COP-Cl promote enantioselective cyclization of E- and Z-configured allylic bis-trichloroacetimidates to highly enantioenriched 2-trichloromethyl-4-vinyloxazoline. This represents an exclusive example for olefin amination in high yield and enantioselectivity with trichloroacetimidate as the N-nucleophile by using a cationic palladium(II) complex as a catalyst providing an easy-to-deprotect enantioenriched vinylglycinol derivative.
Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia.
Ansis
A
Maleckis
Kristine
K
Klimovica
Aigars
A
Jirgensons
D000081:Acetamides / Q000737:chemistry*; D002384:Catalysis; D062845:Chloroacetates / Q000737:chemistry*; D003500:Cyclization; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
C000589593:4-vinyl-2-trichloromethyloxazoline; D000081:Acetamides; D062845:Chloroacetates; D010080:Oxazoles; D010165:Palladium; C009528:trichloroacetamide; D005998:Glycine