Abstract: The hydrolysis of alkyl enol ethers to their corresponding carbonyl compounds proceeds by acid-catalyzed, rate-determining protonation on the/?-carbon to form an oxocarbonium ion intermediate (Kresge, AJ; Chang, YJ Chem. SOC. B 1967, 53). Antibody 14D9 (anti-1) catalyzes the hydrolysis of enol ethers 4 and 5 with very high enantioselectivity of protonation (Reymond, J.-L.; Janda, KD; Lerner, RA J. Am. Chem. SOC. 1992, 114, ...
