Steric Effects on the Stereochemistry of Old Yellow Enzyme??Mediated Reductions of Unsaturated Diesters: Flipping of the Substrate within the Enzyme Active Site …

…, A Manfredi, D Monti, F Parmeggiani

Index: Brenna, Elisabetta; Gatti, Francesco G.; Manfredi, Alessia; Monti, Daniela; Parmeggiani, Fabio Advanced Synthesis and Catalysis, 2012 , vol. 354, # 14-15 p. 2859 - 2864

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Citation Number: 15

Abstract

Abstract The ene-reductase-mediated reduction of the carbon-carbon double bond of some alkyl 2-substituted butenedioates was investigated. The stereochemical outcome of the reaction was found to be influenced by steric effects. Ethyl and butyl citraconates were converted into the corresponding alkyl (R)-2-methylsuccinates with excellent enantioselectivity, whereas ethyl and butyl mesaconates were completely unreactive. ...