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 using 1-phenylethylamine- and 1-(1-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 nitrogen are easily accessible in both enantiomeric forms, and were found to induce good enantioselectivity in the present reaction.
Aoki
K
K
Graduate School of Pharmaceutical Sciences, University of Tokyo, Japan.
Koga
K
K
D000577:Amides; D003510:Cyclohexanes / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008956:Models, Chemical; D010627:Phenethylamines / Q000737:chemistry*; D011522:Protons; D013237:Stereoisomerism
D000577:Amides; D003510:Cyclohexanes; D010627:Phenethylamines; D011522:Protons; C054362:tert-butylcyclohexane; D008094:Lithium