Asymmetric organic reactions, II. Partial kinetic resolution of the grignard reagent from 1-chloro-2-phenylbutane

✍ Scribed by James D. Morrison; Adam Tomash; R.W. Ridgway

• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 171 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)87749-2

✦ Synopsis

The Grignard reagent from racemic l-chloro-2-phenylbutane has been partially resolved by allowing it to react with less than one equivalent of one of several readily available chiral ketones. Reaction with approximately 0.5 equivalents(2) of (+)-camphor, (-)-fenchone, (-)-menthone or (+)-3-methylcyclohexanone led to more rapid consumption of the Grignard reagent having the R configuration as evidenced by the fact that carbonation of the unreacted Grignard reagent gave 3-phenylpentanoic acid enriched in the & enantiomer. As expected the enantiomeric purity of the acid increased when the Grignard reagent was allowed to react with 0.75 equivalents (2) of ketone.