Exploiting continuous processing for challenging diazo transfer and telescoped copper-catalyzed asymmetric transformations
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Date
2021-08-11
Authors
Crowley, Daniel C.
Brouder, Thomas A.
Kearney, Aoife M.
Lynch, Denis
Ford, Alan
Collins, Stuart G.
Maguire, Anita R.
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
Published Version
Abstract
Generation and use of triflyl azide in flow enables efficient synthesis of a range of α-diazocarbonyl compounds, including α-diazoketones, α-diazoamides, and an α-diazosulfonyl ester, via both Regitz-type diazo transfer and deacylative/debenzoylative diazo-transfer processes with excellent yields and offers versatility in the solvent employed, in addition to addressing the hazards associated with handling of this highly reactive sulfonyl azide. Telescoping the generation of triflyl azide and diazo-transfer process with highly enantioselective copper-mediated intramolecular aromatic addition and C–H insertion processes demonstrates that the reaction stream containing the α-diazocarbonyl compound can be obtained in sufficient purity to pass directly over the immobilized copper bis(oxazoline) catalyst without detrimentally impacting the catalyst enantioselectivity.
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Keywords
Triflyl azide , Regitz-type diazo transfer , Deacylative/debenzoylative diazo transfer , α-diazocarbonyl compounds , α-diazoketones , α-diazoamides , α-diazosulfonyl ester
Citation
Crowley, D. C., Brouder, T. A., Kearney, A. M., Lynch, D., Ford, A., Collins, S. G. and Maguire, A. R. (2021) 'Exploiting continuous processing for challenging diazo transfer and telescoped copper-catalyzed asymmetric transformations', Journal of Organic Chemistry. doi: 10.1021/acs.joc.1c01310