Abstract

The conversion of glucal derived donor–acceptor cyclopropanes to acetals by TiCl 4 mediated ring opening and alcohol trapping is described. Good selectivity for the alpha anomer and yields near 90% are consistently observed with aliphatic, benzylic and allylic alcohols, phenols and thiophenols. The utility of this method to prepare oligosaccharides through intermediate O, S-acetals is illustrated.

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