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A rare example of beta- over gamma-C-H selectivity during Rh-catalysed sulfamate ester cyclisation is presented; from derivatives of 1,6-anhydro-beta-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-->sigma*(CH) interactions may be a key controlling factor.

Original publication

DOI

10.1039/c0ob00113a

Type

Journal article

Journal

Org Biomol Chem

Publication Date

07/10/2010

Volume

8

Pages

4246 - 4248