80997-51-9Relevant academic research and scientific papers
Formation, Electrophilic Substitution, and Formal 3 + 2 Cyclization of (2-Carbamoylallyl)lithium Reagents
Beak, Peter,Wilson, Kenneth D.
, p. 4627 - 4639 (2007/10/02)
Directed β'-lithiations of α,β-unsaturated amides and reactions of the resulting (2-carbamoylallyl)lithium reagents with electrophiles are reported.Treatment of (E)-N.N-diisopropyl-2-methyl-2-butenamide (5) provides (E)-2-(N,N-diisopropylcarbamoyl)-3-met
β' Metalation of α,β-Unsaturated Tertiary Amides
Kempf, Dale J.,Wilson, Kenneth D.,Beak, Peter
, p. 1610 - 1612 (2007/10/02)
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.
