Abstract
AbstractInCl3 catalyzes a facile stereoselective 1,3‐migration of allylic ethers of glycals to afford 2‐C‐methylene‐ and 2,3‐unsaturated‐α‐O‐glycosides in high yields. The reaction is rapid (10 min), requires only 20 mol‐% of the catalyst, and is compatible with acid‐labile functional groups such as epoxides and acetals. This methodology provides a convenient alternative to the Ferrier rearrangement. A direct synthesis of an α,α‐(1→1)‐linked disaccharide derivative by a domino process is also reported.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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