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Intramolecular Benzoin Reaction Catalyzed by Benzaldehyde Lyase from Pseudomonas Fluorescens Biovar I
Author(s) -
Hernández Karel,
Parella Teodor,
Petrillo Giovanna,
Usón Isabel,
Wandtke Claudia M.,
Joglar Jesús,
Bujons Jordi,
Clapés Pere
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201702278
Subject(s) - benzaldehyde , intramolecular force , benzoin , pseudomonas fluorescens , chemistry , biovar , catalysis , alkyl , medicinal chemistry , ether , organic chemistry , stereochemistry , biology , biochemistry , bacteria , gene , genetics
Intramolecular 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 OCH 3 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.