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Intramolecular Benzoin Reaction Catalyzed by Benzaldehyde Lyase from Pseudomonas Fluorescens Biovar I

AuthorsHernández Sánchez, Karel ; Parella, T.; Petrillo, Giovanna ; Usón, Isabel ; Wandtke, Claudia M.; Joglar Tamargo, Jesús ; Bujons, Jordi; Clapés Saborit, Pere
Keywordsasymmetric catalysis
C−C coupling
Issue Date2-May-2017
CitationAngewandte Chemie - International Edition 56 (19): 5304-5307 (2017)
AbstractIntramolecular benzoin reactions catalyzed by benzaldehyde lyase from Pseudomonas fluorescens biovar I (BAL) are reported. The structure of the substrates envisaged for this reaction consists of two benzaldehyde derivatives linked by an alkyl chain. The structural requirements needed to achieve the intramolecular carbon–carbon bond reaction catalyzed by BAL were established. Thus, a linker consisting of a linear alkyl chain of three carbon atoms connected through ether-type bonds to the 2 and 2′ positions of two benzaldehyde moieties, which could be substituted with either Cl, Br, or OCH3 at either the 3 and 3′ or 5 and 5′ positions, were suitable substrates for BAL. Reactions with 61–84 % yields of the intramolecular product and ee values between 64 and 98 %, were achieved. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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