Studies on the stereoselective reduction of α-fluoro ketone containing pyridine ring

Abstract

Electrofluorination is very useful method in introducing fluoro atom into organic compounds. In this paper, α-fluoro carbonyl compounds are based on mercapto pyridine carboxylic acid derivatives. However, useful reduction of mercpato pyridyl α-fluoro ketone has not been known up to this time. Herein, we intend to say that appropriate reaction condition is very important in obtaining good isomeric ratio of organic fluorine alcohol in better yield and enhanced stereoselectivity. In our work, product 27 as an example was synthesized and then reduced by various reduction combinations. Besides, plausible reduction pathway was studied by comparative experiments. As a result of these experiments, it was discovered that nitrogen atom and sulfur group of 27 are essential in determining stereoselectivity.