Studies on the Diels-Alder adduct from cyclopentadiene and p-benzoquinone: Biotransformation, enantiomeric excess and absolute configuration

Felipe Camargo Braga, Dênis P. de Lima, Adilson Beatriz, Felicia M. Ito

Abstract


The use of microorganisms or isolated enzymes in synthetic routes has been extensively used by industry and academic research. A great advantage of biotransformation in a synthetic route is highly regio- and enatiosselective control, which can be achieved through microbial catalyzed reaction. Biotransformation is one of the most efficient methods in a production of high purity optical compounds and development of efficient routes for target molecules. Biotransformation by Mucor ramosissimus of enedione 1 gave the keto-alcohol (-)-2 with enantiomeric excess (ee)>99,9% (determined by 1H NMR with [(+)-Eu(hfc)]3) and their epimer (-)-3. Determination of the absolute configuration of epimer (-)-3 was accomplished by controlled reaction and measuring of optical rotation (scheme 1). The fungus M. ramosissimus is a promising species to perform desymmetrization of diketones with high enantioselectivity.


Keywords


Diels-Alder adduct; chiral shift reagent; absolute configuration; biotransformation

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Orbital: The Electronic Journal of Chemistry (e-ISSN 1984-6428) is a quarterly scientific journal published by the Institute of Chemistry of the Universidade Federal de Mato Grosso do Sul, Brazil. Orbital is a peer-reviewed, open-access journal.