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Numerous methods for the stereoselective synthesis of chiral compounds exist in the literature, which use chiral templates or catalysts. Only in a limited number of cases have achiral catalysts been shown to significantly influence the stereochemical outcomes of reactions. Previous studies in our laboratories have revealed the achiral acyl-transfer catalyst pyridine to alter the stereochemical outcome of the reaction of racemic trans-2-substituted cyclohexanols with racemic 2-chloropropionyl chloride and cause a reversal of diastereoselectivity. The current paper presents the application of the reaction scheme to a wider number of substrates and reveals the importance of the heteroatom in the trans-2-substituent.

Acylation of trans-2-substituted cyclohexanols: the impact of substituent variation on the pyridine-induced reversal of diastereoselectivity