Rearrangement of N-Allyl-α,α-dichloroamides, β- or γ- Functionalized, to Substituted Analogues of the γ-Aminobutyric Acid (GABA)

Abstract

The rearrangement of γ-chlm, β-hydroxy or β-vmyl N-allyl-N-benzyl-α,α-dichlorocarboxyamides to γ-aminobutynic acid analogues is efficiently promoted by CuCI\N,N,N′,N′-tetramethylethylendiamine. With the β-vinyl functionalization a tandem radical-radical reaction, yieldmg 3-aza-2-oxo-bicyclo[3,3,0]actatre adducts, is also observed.