β' Metalation of α,β-Unsaturated Tertiary Amides

Article abstract of DOI:10.1021/jo00347a060

Novel β' metalations of the α,β-unsaturated tertiary amides N,N-diisopropyl-1-cyclohexenecarboxamide (3), (E)-N,N-diisopropyl-2-methyl-2-butenamide (7), and N,N-diisopropyl-6-(trimethylsilyl)-1-cyclohexenecarboxamide (10) are reported.Additions of the β'-lithio-α,β-unsaturated tertiary amides 4, 8, and 11 to a variety of electrophiles, including in the case of 8 subsequent formation of five-membered rings, illustrate the value of this approach for achieving substitution at the β' position of α,β-unsaturated carboxylic acid derivatives.