Catalytic Enantioselective α-Fluorination of Carbonyl Compounds Using Chiral Transition Metal Complexes

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概要

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• Two catalytic systems were developed for efficient catalytic enantioselective α-fluorination reactions of carbonyl compounds. Cationic Pd complexes were found to be effective for fluorination of active methine and methylene compounds, and various substrates including β-ketoesters, β-ketophosphonates, and other related compounds were fluorinated in environmentally friendly alcoholic solvents (up to 99% ee). This system was also applicable to the reaction of 3-substituted oxindole derivatives. In addition, we succeeded in developing a novel trinary system NiCl<SUB>2</SUB>-binap/R<SUB>3</SUB>SiOTf/2, 6-lutidine for the reaction of less acidic α-aryl acetic acid derivatives, and the desired reaction proceeded smoothly to give the corresponding monofluorinated compounds in a highly enantioselective manner (up to 88% ee). Our fluorination reactions are versatile, being applicable to stereoselective synthesis of chiral fluorinated analogues of fundamental building blocks and catalytic asymmetric synthesis of BMS204352, a promising agent for the treatment of stroke.

• 社団法人 有機合成化学協会の論文
• 2007-11-01

著者

• Sodeoka Mikiko

  Synthetic Organic Chemistry Laboratory Riken

• HAMASHIMA Yoshitaka

  Synthetic Organic Chemistry Laboratory, RIKEN

• Hamashima Yoshitaka

  Synthetic Organic Chemistry Laboratory Riken

関連論文

• Catalytic Enantioselective α-Fluorination of Carbonyl Compounds Using Chiral Transition Metal Complexes

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