Exploring F/CF3 substituted oxocarbenium ions for the diastereoselective assembly of highly substituted tetrahydrofurans

Abstract

Understanding the influence of emerging fluorinated motifs is of a crucial importance in the context of the exponentially growing exploitation of fluorine in many fields. Herein, we report on the dramatic effect of a local partial charge inversion by replacing a CHCH₃ group by a CFCF₃. This strategy allows the diastereoselective reduction of 5-membered ring oxocarbenium ions to access highly substituted tetrahydrofurans.