Generation and Ring Opening of Aziridines in Telescoped Continuous Flow Processes
Nathanael Hsueh, Guy J. Clarkson and Michael Shipman*
*Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, U.K., Email: m.shipmanwarwick.ac.uk
N. Hsueh, G. J. Clarkson, M. Shipman, Org. Lett., 2015, 17, 3632-3635.
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A simple flow method enables the preparation of various N-sulfonyl aziridines from 1,2-amino alcohols. 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 avoids the handling of potentially hazardous aziridine intermediates.
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Wenker Synthesis, Flow Chemistry