Abstract
The propionates (R)‐5 and (R)‐6 which are derived from the readily available chiral auxiliary reagent (R)‐triphenylglycol (4) have been applied in stereoselective aldol reactions. Whereas the enolate 7 and the silyl ketene acetal 12, both generated from the ester (R)‐6, display only moderate diastereoselectivity when treated with benzaldehyde, ß‐hydroxyesters 8b and 16a, b are formed in diastereomeric ratios up to 95:5 (ratio of the main product to the sum of all other stereoisomers) when the propionate (R)‐5 is subsequently deprotonated, transmetalated into the zirconium enolate and allowed to react with aldehydes. Alkaline hydrolysis or reduction with LiAlH4 enables the conversion of the adducts 8a and 16a
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