Origins of diastereoselectivity in the alkylation of N-substituted lactams and amides derived from optically active aminoalcohols

Article abstract of DOI:10.1016/0957-4166(96)00374-6

The origins of diastereoselectivity in the alkylation of lactams 1a and 1b and amides 6a and 6b are discussed. A rigid intermediate in which the pyramidalized amide nitrogen chelated the alkoxide lithium cation is invoked. Further experiments conducted wi