Issue 12, 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

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

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
26 Jan 2017
Accepted
28 Feb 2017
First published
28 Feb 2017

Org. Biomol. Chem., 2017,15, 2609-2628

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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