A novel class of β-lactam derivatives of 1-aminophosphonates
was synthesized by Staudinger [2+2] cycloaddition
reaction of ketenes with imines derived from 1-aminophosphonates. Treatment
of aromatic aldehydes with ammonia and diethyl phosphite followed
by a reaction with ketenes, which are generated from the appropriate
acid chloride and a tertiary amine, gave a novel class of β-lactam
derivatives of 1-aminophosphonates. The major or, in some cases,
sole product of the cycloaddition is the cis-β-lactam.
1-aminophosphonates - β-lactams - ketenes - imines - [2+2]-cycloaddition
reaction