Antibody-catalyzed hydrolysis of enol ethers. 2. Structure of the antibody-transition state complex and origin of the enantioselectivity

GK Jahangiri, JL Reymond

Index: Jahangiri, Guiti K.; Reymond, Jean-Louis Journal of the American Chemical Society, 1994 , vol. 116, # 25 p. 11264 - 11274

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Citation Number: 43

Abstract

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, ...