Inexpensive Reagents for the Synthesis of Amides from Esters and for Regioselective Opening of Epoxides

Article abstract of DOI:10.1021/jo00048a011

Lithium aluminum amides , 6a-6d, easily prepared in Et2O or THF from 1 equiv of LiAlH4 and 5 equiv of amine, proved to be efficient reagents for the synthesis of secondary amides from esters (ca. 100 percent with unhindered amines and 92 percent with t-BuNH2).They also open aryl epoxides with very high regioselectivity to give 97-98 percent of the β-amino-α-arylethanols (corresponding to the SN₂ mechanism).