A regioselective synthesis of 3-chloro-3-deoxy sugars (6)–(10) has been achieved by trans-diaxial cleavage of the oxiran ring in 2,3-anhydro sugars (1)–(5) with dichlorobis(benzonitrile)palladium(II). The complex does not cause epoxide migration and may be employed in the presence of acid-sensitive functions.
N. Afza, A. Malik and W. Voelter, J. Chem. Soc., Perkin Trans. 1, 1983, 1349 DOI: 10.1039/P19830001349
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