Acyclic Stereoselection in the Alkylation of Chiral Dipole-Stabilized Organolithiums: A Self-Immolative Chirality Transfer Process for the Synthesis of Primary Amines

Article abstract of DOI:10.1021/jo00274a004

A comparison of 1,3- and 1,5-asymmetric induction shows the former to have far greater selectivity in the methylation of chiral dipole-stabilized organolithiums.The asymmetric alkylation of N-benzyloxazolidinones is employed as the key step in a new synthesis of primary amines by asymmetric alkylation α to nitrogen.