Aldol reaction of butane-2,3-diacetal protected methyl glycerate

The addition of aldehydes to butane-2,3-diacetal protected glycerates has been investigated. The reaction was shown to be diastereoselective by 1H NMR spectroscopy thus confirming the ability of the diacetal to influence the stereochemical outcome of the new stereogenic center, the configuration of which was determined by Mosher’s ester analysis.

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(2R)-2-(Hydroxy-phenyl-methyl)-5,6-dimethyl-5,6-dimethoxy-[1,4]-dioxane-2-carboxylic acid methyl esterC17H24O7[α]D = −107.1 (c 0.7, CHCl3)Source of chirality: butane-2,3-diacetal frameworkAbsolute configuration: (2R)

(2S)-2-(Hydroxy-phenyl-methyl)-5,6-dimethyl-5,6-dimethoxy-[1,4]-dioxane-2-carboxylic acid methyl esterC17H24O7[α]D = −76.2 (c 0.6, CHCl3)Source of chirality: butane-2,3-diacetal frameworkAbsolute configuration: (2S)