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Issue 19, 2010
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Inverted regioselectivity of C–H amination: Unexpected oxidation at β- rather than γ-C–H

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Abstract

A rare example of β- over γ-C–H selectivity during Rh-catalysed sulfamate ester cyclisation is presented; from derivatives of 1,6-anhydro-β-D-mannopyranose, five-membered sulfamidates were formed in preference to the typical six-membered oxathiazinane intramolecular insertion products. A 3D structure of sulfamate 1 helps to rationalise this unusual selectivity and analyses suggest that n→σ*(CH) interactions may be a key controlling factor.

Graphical abstract: Inverted regioselectivity of C–H amination: Unexpected oxidation at β- rather than γ-C–H

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Publication details

The article was received on 12 May 2010, accepted on 05 Jul 2010 and first published on 22 Jul 2010


Article type: Communication
DOI: 10.1039/C0OB00113A
Citation: Org. Biomol. Chem., 2010,8, 4246-4248
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    Inverted regioselectivity of C–H amination: Unexpected oxidation at β- rather than γ-C–H

    F. J. Wyszynski, A. L. Thompson and B. G. Davis, Org. Biomol. Chem., 2010, 8, 4246
    DOI: 10.1039/C0OB00113A

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