Factors controlling regioselectivity in deprotonations of unsymmetrical ketimines

…, DE Bergbreiter, M Newcomb

Index: Smith, J. Kirk; Bergbreiter, David E.; Newcomb, Martin Journal of the American Chemical Society, 1983 , vol. 105, # 13 p. 4396 - 4400

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Citation Number: 29

Abstract

Abstract: The regioselectivity of deprotonation of equilibrium EZ mixtures of the benzyl, n- butyl, cyclohexyl, phenyl, and tert-butyl imines of 2-butanone by lithium diisopropylamide (LDA) in tetrahydrofuran has been shown to be a function of both the nitrogen substituent and the temperature of the deprotonation reaction. High regioselectivity at either the methyl or methylene substituent could be obtained for all imines except the benzyl and n-butyl ...