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2005
Halogenation
O 0235
Relative Electrophilic Fluorinating Power as Assayed by Competitive Catalytic
Reactions. — With a view to find the most active fluorinating reagent
09- 036 Halogenation
compatible with the chiral titanium catalyst, competitive halogenations are performed
with ketoester (I) using equimolar amounts of N-chlorosuccinimide and seven different
N—F derivatives already known to exhibit the desired reactivity with β-keto esters.
SelectfluorTM and AccufluorTM are the most powerful fluorinating reagents tested,
whereas neutral amine derivatives act as very slow fluorinating compounds. The enantioselectivities concerning fluorination of ester (I) with SelectfluorTM alone and chlorination with NCS alone affords compounds (II) and (III) with 71 and 59% e.e., respectively. The combination of both halogenating agents leads to little changes in the enantioselectivites of both compounds. — (TOULLEC, P. Y.; DEVILLERS, I.; FRANTZ,
R.; TOGNI*, A.; Helv. Chim. Acta 87 (2004) 10, 2706-2711; Dep. Chem., Swiss Fed.
Inst. Technol., ETH-Hoenggerberg, CH-8093 Zuerich, Switz.; Eng.) — Klein
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