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Issue 12, 2017
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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

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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.

Graphical abstract: 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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Submitted
26 Jan 2017
Accepted
28 Feb 2017
First published
28 Feb 2017

Org. Biomol. Chem., 2017,15, 2609-2628
Article type
Paper

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

A. E. Shiely, C. N. Slattery, A. Ford, K. S. Eccles, S. E. Lawrence and A. R. Maguire, Org. Biomol. Chem., 2017, 15, 2609
DOI: 10.1039/C7OB00214A

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