Stereoselective reactions. XXXII. enantioselective deprotonation of 4-tert-butylcyclohexanone by fluorine-containing chiral lithium amides derived from 1-phenylethylamine and 1-(1-naphthyl)ethylamine

Enantioselective deprotonation of 4-tert-butylcyclohexanone was examined us ing 1-phenylethylamine- and 1-(l-naphthyl)ethylamine-derived chiral lithium amides having an alkyl or a fluoroalkyl substituent at the amide nitrogen. The lithium amides having a 2,2,2-trifluoroethyl group on the amide nitrog en are easily accessible in both enantiomeric forms, and were found to indu ce good enantioselectivity in the present reaction.