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Restriction lift date:2018-03-08
Citation:McCaw, P. G., Buckley, N. M., Eccles, K. S., Lawrence, S. E., Maguire, A. R. and Collins, S. G. (2017) 'Synthesis of cyclic alpha-diazo-beta-keto sulfoxides in batch and continuous flow', Journal of Organic Chemistry, 82(7), pp. 3666-3679. doi:10.1021/acs.joc.7b00172
Diazo transfer to beta–keto sulfoxides to form stable isolable alpha-diazo-beta-keto sulfoxides has been achieved for the first time. Both monocyclic and benzofused ketone derived beta-keto sulfoxides were successfully explored as substrates for diazo transfer. Use of continuous flow leads to isolation of the desired compounds in enhanced yields relative to standard batch conditions, with short reaction times, increased safety profile and potential to scale up.
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