Asymmetrical synthesis of fluorinated 2-(pyridin-2-yl) alkylamine from fluoromethyl sulfinyl imines and 2-alkylpyridines

A novel strategy was developed to synthesize fluorinated 2-(pyridin-2-yl) alkylamines via condensation of 2-alkylpyridines and chiral fluoromethyl N-tert-butyl sulfinyl imines with good diastereo-control and good chemical yields. The chiral N-tert-butyl sulfinyl auxiliary can be easily removed under mild acidic condition at room temperature. The application of this strategy was demonstrated in the synthesis of a fluorine-containing pesticide candidate. (C) 2015 Elsevier Ltd. All rights reserved.