The synthesis of α-amino-γ-substituted adipic acids: stereoelectronic effects during the 1,4-addition of organocuprates to methyl N-tert-butoxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylate

Abstract

The α,β-unsaturated lactam 3 was submitted to 1,4-addition of organocuprate reagents R₂CuLiI₂ (R = Me, Bu or Ph) to provide the 4-substituted compounds 5a–c, 6a–c as a mixture of diastereomers; these intermediates were then transformed into the corresponding α-amino-γ-substituted adipic acids 7a–c, 8a–c.