Isobomylamine imine anion from cyclohexanone

The synthetic implications of carbon-carbon bond formation via imine anions gained additional significance with the first report by Horeau of asymmetric induction in the alkylation of the anion derived from isobomylamine and cyclohexanone. However, the degree of stereochemical control in the formation of 2-meAylcyclohexanone by this process (72% ee) was below the synthetically useful level. Additionally, incorporation of other alkyl groups afforded even lower levels of asymmetric induction. Further studies by Yamada with a variety of chiral amines did not improve on these results. ... 

---