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InCl 3 ‐Catalyzed Rapid 1,3‐Alkoxy Migration in Glycal Ethers: Stereoselective Synthesis of Unsaturated α‐ O ‐Glycosides and an α,α‐(1→1)‐Linked Disaccharide
Author(s) -
Nagaraj Paramathevar,
Ramesh Namakkal G.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800453
Subject(s) - chemistry , stereoselectivity , disaccharide , allylic rearrangement , glycal , catalysis , domino , alkoxy group , organic chemistry , glycoside , stereochemistry , alkyl
InCl 3 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)