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Blocking Fluorine Substitution in Biotransformation of Nortricyclanyl N ‐Phenylcarbamates with Beauveria bassiana
Author(s) -
Haufe Günter,
Wölker Dörthe
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.200200647
Subject(s) - chemistry , alicyclic compound , hydroxylation , biotransformation , beauveria bassiana , ring (chemistry) , stereochemistry , biocatalysis , fluorine , organic chemistry , enzyme , reaction mechanism , botany , biological pest control , biology , catalysis
The biotransformation of tricyclo[2.2.1.0 2,6 ]hept‐3‐yl N ‐phenylcarbamate ( 8 ) by a standard procedure using Beauveria bassiana gave a 7:1 mixture of optically active exo , exo ‐ and exo , endo ‐5‐hydroxytricyclo[2.2.1.0 2,6 ]hept‐3‐yl N ‐phenylcarbamates 15 and 16 in 19% isolated yield. No ring opening of the three‐membered ring was observed. Substitution with a fluorine atom at the 5‐ endo ‐ or 5‐ exo ‐position prevented hydroxylation of any alicyclic position of the molecules, p ‐hydroxylation of the aromatic ring occurring to a small extent instead. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)