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Synthesis of Fluorinated Cycloalkyl N ‐Phenylcarbamates and Their Microbial Defluorination/Oxygenation by Beauveria bassiana
Author(s) -
Haufe Günter,
Pietz Sylke,
Wölker Dörthe,
Fröhlich Roland
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200200648
Subject(s) - chemistry , hydroxylation , beauveria bassiana , ketone , substituent , geminal , organic chemistry , stereochemistry , medicinal chemistry , enzyme , botany , biological pest control , biology
Abstract Earlier investigations showed that cycloalkyl N ‐phenylcarbamates were hydroxylated by the fungus Beauveria bassiana predominantly in the 4‐position relative to the electron‐rich substituent. In cases involving fluorinated methylene groups potentially capable of hydroxylation, however, defluorination and formation of a ketone was observed. The formation of the ketone can be explained by primary hydroxylation to form an unstable geminal fluorohydrin, which is subsequently dehydrofluorinated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)