One‐Pot Synthesis of N‐tert‐Butylsulfinylimines and Homoallylamine Derivatives from Epoxides

Abstract

The reaction of epoxides with tert‐butanesulfinamide in the presence of a Lewis acid, such as erbium triflate or boron trifluoride–diethyl ether, in THF as solvent, under microwave or thermal activation, produces N‐tert‐butylsulfinylimines in reasonable yields. Aromatic and gem‐disubstituted and trisubstituted alkyl epoxides performed better than mono‐alkyl‐substituted compounds. After imine formation, a subsequent indium‐promoted allylation can be carried out in the same reaction flask in a single synthetic operation leading to homoallylamine derivatives with generally high yields.