Enantioselective copper catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent

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Enantioselective copper catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent

Shiely, Amy E.; Slattery, Catherine N.; Ford, Alan; Eccles, Kevin S.; Lawrence, Simon E.; Maguire, Anita R.
Date: 2017-02-28
Copyright: © 2017, the Authors. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic and Biomolecular Chemistry. To access the final edited and published work see http://dx.doi.org/10.1039/C7OB00214A
Full text restriction information: Access to this article is restricted until 12 months after publication by request of the publisher.
Restriction lift date: 2018-02-28
Citation: Shiely, A. E., Slattery, C. N., Ford, A., Eccles, K. S., Lawrence, S. E. and Maguire, A. R. (2017) ‘Enantioselective copper catalysed intramolecular C–H insertion reactions of α-diazo-β-keto sulfones, α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones; the influence of the carbene substituent’, Organic and Biomolecular Chemistry, 15, pp. 2609-2628. doi:10.1039/C7OB00214A
Published Version: 10.1039/C7OB00214A

Abstract:

Enantioselectivities in C–H insertion reactions, employing the copper-bis(oxazoline)-NaBARF catalyst system, leading to cyclopentanones are highest with sulfonyl substituents on the carbene carbon, and furthermore, the impact is enhanced by increased steric demand on the sulfonyl substituent (up to 91%ee). Enantioselective intramolecular C–H insertion reactions of α-diazo-β-keto phosphine oxides and 2-diazo-1,3-diketones are reported for the first time.

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