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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Accepted Version
Date
2017-02-28
Authors
Shiely, Amy E.
Slattery, Catherine N.
Ford, Alan
Eccles, Kevin S.
Lawrence, Simon E.
Maguire, Anita R.
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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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Keywords
C–H insertion , Cyclopentanone , Sulfonyl substituent
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
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© 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