Organic Chemistry Portal

Abstracts

Search:

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.

DOI: 10.1021/acs.orglett.5b01777 (free Supporting Information)


see article for more reactions

Abstract

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