Regioselective C-O bond cleavage reactions of acetals
Journal
Pure and Applied Chemistry
Journal Volume
68
Journal Issue
3
Pages
635-638
Date Issued
1996
Author(s)
Luh, T.-Y.
Abstract
Reactions of acetonide derivatives of monosaccharides with the Grignard reagent in benzene afford the corresponding monosaccharide derivatives having only one free hydroxy group. 1,4-di-alkoxy-(2S,3S)-2,3-butanediols are obtained from the reactions of 2S,3S-threitol bisketals with Grignard reagents or with LiAlH4/AlCl3. The reactions of benzylic acetals prepared from 1,4-dialkoxy-(2S,3S)-2,3-butanediols and aromatic aldehydes, with aryl or secondary or sterically hindered Grignard reagents give the corresponding ring-opening products in high diastereoselectivity. Other synthetic applications of such tunable chiral diols are briefly described.
SDGs
Type
journal article