Organic Chemistry Portal



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:

N. Hsueh, G. J. Clarkson, M. Shipman, Org. Lett., 2015, 17, 3632-3635.

DOI: 10.1021/acs.orglett.5b01777

see article for more reactions


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.

see article for more examples

Key Words

Wenker Synthesis, Flow Chemistry

ID: J54-Y2015