Copper mediated, heterogeneous, enantioselective intramolecular Buchner reactions of a-diazoketones using continuous flow processing

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Copper mediated, heterogeneous, enantioselective intramolecular Buchner reactions of a-diazoketones using continuous flow processing

Crowley, Daniel C.; Lynch, Denis; Maguire, Anita R.
Date: 2018-03-15
Copyright: © 2017 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.joc.8b00147
Full text restriction information: Access to this article is restricted until 12 months after publication by request of the publisher.
Restriction lift date: 2019-03-15
Citation: Crowley, D. C., Lynch, D. and Maguire, A. R. (2018) 'Copper mediated, heterogeneous, enantioselective intramolecular Buchner reactions of α-diazoketones using continuous flow processing', The Journal of Organic Chemistry, In Press, doi: 10.1021/acs.joc.8b00147
Published Version: 10.1021/acs.joc.8b00147

Abstract:

Enantioselective intramolecular Buchner reactions of α-diazoketones can be effected using heterogeneous copper−bis(oxazoline) catalysts in batch or using continuous flow processing in up to 83% ee. The catalyst can be reused up to 7 times without loss of activity. For α-diazoketones 3 and 4, the enantioselection achieved in flow with the immobilized catalyst was comparable with the standard homogeneous catalyzed process.

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