Generation and Ring Opening of Aziridines in Telescoped Continuous Flow Processes

A simple method for
the preparation of a variety of N-sulfonyl aziridines
(10 examples) from 1,2-amino alcohols under
continuous flow conditions is described. Using flow based methods,
the aziridines can be further ring opened with oxygen, carbon, and
halide nucleophiles or ring expanded to imidazolines by Lewis acid
promoted reaction with nitriles. Telescoping the aziridine generation
and ring opening steps together in a microfluidic reactor allows the
chemistry to be undertaken with limited exposure to the potentially
hazardous aziridine intermediates.