Stereoselective alkylation of N-Boc-protected-5-substituted delta-lactams: synthesis of alpha, delta-disubstituted delta-amino acids

ABSTRACT

N-Boc-protected-5-substituted delta-lactams were readily prepared from the corresponding beta 3-amino acids. Alkylation reactions of their Na enolates with various electrophiles proceeded in high yields with high facial selectivity. The structure of the alkylation products was confirmed by single-crystal X-ray analysis. This method provides a fast access to optically active alpha, delta-disubstituted delta-amino acids.