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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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Publication details

The article was received on 26 Jan 2017, accepted on 28 Feb 2017 and first published on 28 Feb 2017


Article type: Paper
DOI: 10.1039/C7OB00214A
Citation: Org. Biomol. Chem., 2017,15, 2609-2628
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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

    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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