Dipole-Stabilized Carbanions: Secondary (α-Lithioalkyl)alkylamine Synthetic Equivalents from N,N-dialkyl-2,2-diethylbutyramides

Article abstract of DOI:10.1021/jo00334a052

Lithiation of N,N-dialkyl-2,2-diethylbutyramides adjacent to nitrogen followed by addition to an aldehyde or ketone, an acid-driven nitrogen to oxygen rearrangement, and basis hydrolysis provides secondary (α-lithioalkyl)alkylamine synthetic equivalents.