Abstract
Three racemic a-fluorinated benzyl beta-ketoesters have been synthesized by electrophilic fluorination with Selectfluor(TM). They were submitted to our well established palladium-mediated cascade reaction (deprotection, decarboxylation and protonation of the resulting enolic species) producing optically active alpha-fluoro ketones. With benzyl 2-fluoro-1-tetralone-2-carboxylate as substrate, ...
Abstract
Three racemic a-fluorinated benzyl beta-ketoesters have been synthesized by electrophilic fluorination with Selectfluor(TM). They were submitted to our well established palladium-mediated cascade reaction (deprotection, decarboxylation and protonation of the resulting enolic species) producing optically active alpha-fluoro ketones. With benzyl 2-fluoro-1-tetralone-2-carboxylate as substrate, (S)-(-)-2-fluoro-1-tetralone with up to 65% enantiomeric excess was obtained using quinine as the chiral base and Pd/C type 807104 from Merck as the heterogeneous catalyst. (C) 2003 Elsevier Ltd. All rights reserved.
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