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Generation and ring opening of aziridines in telescoped continuous flow processes
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Hsueh, Nathanael, Clarkson, Guy J. and Shipman, Michael (2015) Generation and ring opening of aziridines in telescoped continuous flow processes. Organic Letters, 17 (14). pp. 3632-3635. doi:10.1021/acs.orglett.5b01777 ISSN 1523-7060.
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Official URL: http://dx.doi.org/10.1021/acs.orglett.5b01777
Abstract
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.
Item Type: | Journal Article | ||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Organic Letters | ||||
Publisher: | American Chemical Society | ||||
ISSN: | 1523-7060 | ||||
Official Date: | 9 July 2015 | ||||
Dates: |
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Volume: | 17 | ||||
Number: | 14 | ||||
Page Range: | pp. 3632-3635 | ||||
DOI: | 10.1021/acs.orglett.5b01777 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access |
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