Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids.
A synthetic procedure for the preparation of 4-cyclohexyl-2-methyl-buta-2,3-dienoic acid in the two optically active forms has been developed. Synthesis of the racemic allenoic acid was made by an efficient route with good overall yield. Resolution of the enantiomers was achieved by forming the cinchonidine and cinchonine diastereomeric salt, respectively, and the enantiomers were isolated in up to 95% enantiomeric excess. The absolute configuration of the allenoic acid was determined by X-ray crystallography.
Nyhlén
Jonas
J
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden.
Eriksson
Lars
L
Bäckvall
Jan-E
JE
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis; D000143:Acids / Q000138:chemical synthesis*; D000470:Alkaloids / Q000737:chemistry* / Q000378:metabolism; D002930:Cinchona Alkaloids / Q000737:chemistry; D018360:Crystallography, X-Ray; D055095:Optics and Photonics; D010753:Phosphoranes / Q000737:chemistry; D012492:Salts / Q000378:metabolism*; D013237:Stereoisomerism
D000143:Acids; D000470:Alkaloids; D002930:Cinchona Alkaloids; D010753:Phosphoranes; D012492:Salts; C041622:cinchonidine; C004511:butenolide; D015107:4-Butyrolactone; C010086:cinchonine