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Yufeng Miao, Dr. Edzard M. Geertsema, Pieter G. Tepper, Dr. Ellen Zandvoort and Prof. Dr. Gerrit J. Poelarends Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase ChemBioChem 14

Version of Record online: 9 JAN 2013 | DOI: 10.1002/cbic.201200676

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Exploiting catalytic promiscuity: The proline-based enzyme 4-oxalocrotonate tautomerase (4-OT) promiscuously catalyzes asymmetric Michael-type additions of linear aldehydes—ranging from acetaldehyde to octanal—to trans-β-nitrostyrene in aqueous solvent. The presence of 1.4 mol % of 4-OT effected formation of the anticipated γ-nitroaldehydes in fair to good yields with dr values of up to 93:7 and ee values of up to 81 %.

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