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2004
Oxirane derivatives
R 0030
Effect of α-Fluorination on Asymmetric Epoxidation of trans-Olefins Using
Cyclohexanone Dioxiranes. — Epoxidation of trans-β-methylstyrene
52- 087 α-Fluorinated
(III) and trans-stilbene (V) using chiral dioxiranes derived from both enantiopure diastereomers of α-fluoro cyclohexanones (I) and (II) are studied and compared. In case
of ketones (I) the enantioselectivities are significant higher and all types of ketones produce the same (-)-enantiomer. The results obtained are rationalized by detailed ab initio
calculations. — (SOLLADIE-CAVALLO*, A.; JIERRY, L.; NOROUZI-ARASI, H.;
TAHMASSEBI, D.; J. Fluorine Chem. 125 (2004) 9, 1371-1377; Lab. Stereochim.,
CNRS, Univ. Louis Pasteur, F-67087 Strasbourg, Fr.; Eng.) — M. Paetzel
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