Lithiation of N-Boc-2-methyltetrahydro-1,3-oxazine: A Synthetic Equivalent for 1-Lithio-3-hydroxy-1-propylamine

Article abstract of DOI:10.1021/jo00056a010

A α-metalo amine synthetic equivalent of an unactivated primary amine, 1-lithio-3-hydroxy-1-propylamine (7) is provided by the lithiation of N-Boc-2-methyltetrahydro-1,3-oxazine (8) to give 9 which on reaction with electrophiles and hydrolysis gives derivatives of 1-substituted 3-hydroxy-1-propylamines 10-24.