Consider the reaction between cyclohexanone and the
Chapter 22, Problem 22.111(choose chapter or problem)
Consider the reaction between cyclohexanone and the optically pure amine shown below (J. Org. Chem., 1977, 42, 16631664). (a) Draw the structure of the resulting enamine and discuss how many isomer(s), if any, form in this reaction. (b) When the enamine(s) formed in part a is (are) treated with methyl iodide, followed by aqueous acid, 2-methylcyclohexanone with 83% ee is isolated. Explain the source of the observed enantiomeric excess (as compared with the racemic mixture obtained in 22.110), and identify the enantiomer that predominates. O H H3C N CH3 TsOH H2O +
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