Chain-Elongation of Sugar Aldehydes by Asymmetric Homoaldol Reaction: Introduction of a Functionalized 3-Methyl-Substituted Three-Carbon Unit

Abstract

O-Protected aldehydo-sugars reacted with α-titanated crotyl N,N-diisopropylcarbamate to furnish chain-elongated alk-1-enyl carbamates. These were further functionalized by epoxidation of the double bond and subsequent methanolysis to form methyl 3-C-methyl-3-deoxy-furanosides. Mukaiyama-type addition of benzaldehyde led to tetrasubstituted tetrahydrofurans. All reactions proceeded with high diastereoselectivities and allow for a broad application.

homoaldol reaction - epoxides - (-)-sparteine-mediated metalation - stereoselective synthesis - branched carbohydrates

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