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Issue 38, 2014
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Enantioselective copper catalysed C–H insertion reaction of 2-sulfonyl-2-diazoacetamides to form γ-lactams

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Abstract

The first examples of asymmetric copper-catalysed intramolecular C–H insertion reactions of 2-sulfonyl-2-diazoacetamides are described; trans γ-lactams with up to 82% ee are achieved with the CuCl2-bisoxazoline-NaBARF catalyst system. The reactions generally display high efficiency and high trans selectivity, and also a strong regiochemical preference for insertion to lead to the formation of 5-membered rings over 4-membered rings. In cases where there are competing C–H insertion pathways available, to form sulfolanes or thiopyrans, only the insertion into the amide chain to form γ-lactams is observed. With phenylsulfonyl derivatives, a minor competing C–H insertion pathway leading to β-lactams is seen; interestingly, changing the identity of the copper ligand changes the product ratio of β/γ-lactams. The copper catalysed reactions compare favorably in terms of efficiency and enantioselectivity to the corresponding reactions catalysed by commercially available chiral rhodium catalysts.

Graphical abstract: Enantioselective copper catalysed C–H insertion reaction of 2-sulfonyl-2-diazoacetamides to form γ-lactams

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Publication details

The article was received on 08 Jul 2014, accepted on 14 Aug 2014 and first published on 14 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01430H
Citation: Org. Biomol. Chem., 2014,12, 7612-7628
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    Enantioselective copper catalysed C–H insertion reaction of 2-sulfonyl-2-diazoacetamides to form γ-lactams

    L. A. Clarke, A. Ring, A. Ford, A. S. Sinha, S. E. Lawrence and A. R. Maguire, Org. Biomol. Chem., 2014, 12, 7612
    DOI: 10.1039/C4OB01430H

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