Stereselective Reactions. XXXII. Enantioselective Deprotonation of 4-tert-Butylcyclohexanone by Fluorine-Containing Chiral Lithium Amides Derived from 1-Phenylethylamine and 1-(1-Naphthyl)ethylamine

Abstract

Enantioselective deprotonation of 4-tert-butylcyclohexanone was examined using 1-phenylethylamine- and 1-(1-naphtyl)ethylamite-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 nitrogen are easily accessible in both enantiomeric forms, and were found to induce good enantioselectivity in the present reaction.