Synthesis of fluorinated cycloalkyl N-phenylcarbamates and their microbial defluorination/oxygenation by Beauveria bassiana

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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).