Lithiation of α-Nitrosaminoalkyl Ethers. Synthetic Equivalents of α-Primary Amino Carbanions

Article abstract of DOI:10.1021/jo00162a019

Successful experiments directed toward the C-1 alkylation and hydroxyalkylation of primary amines are reported.Primary amines are converted into their N-nitroso-N-(1-methoxyethyl) derivatives, which are subsequently lithiated and condensed with various electrophiles, denitrosated, and hydrolyzed to produce the desired compounds in good to excellent yields.