Digital Commons Network^™

Acylation Of Trans-2-Substituted Cyclohexanols: The Impact Of Substituent Variation On The Pyridine-Induced Reversal Of Diastereoselectivity, Sven Hackbusch, Andreas H. Franz

College of the Pacific Faculty Articles

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