The. beta.'lithiation of. alpha.,. beta.-unsaturated amides

P Beak, DJ Kempf, KD Wilson

Index: Beak,P.; Kempf,D.J.; Wilson,K.D. Journal of the American Chemical Society, 1985 , vol. 107, p. 4745

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Citation Number: 37

Abstract

Abstract: The sequence of p'lithiation and electrophilic substitution of a,@-unsaturated secondary and tertiary amides is reported to provide a convenient method for selective p'functionalization of a, P-unsaturated acid derivatives. Lithiation with sec-BuLi/TMEDA of N- methyl-1-cyclohexenecarboxamide (19), N-methyl-1-cyclopentenecarboxamide (30), N, N- diisopropyl-1-cyclohexenecarboxamide (36), N, N-diisopropyl-6-(trimethylsilyl)-l- ...