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

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 CHCH 3 group by a CFCF 3 . This strategy allows the diastereoselective reduction of 5-membered ring oxocarbenium ions to access highly substituted tetrahydrofurans. We report on the dramatic effect of a local partial charge inversion by replacing a CHCH 3 group by a CFCF 3 . This strategy allows the diastereoselective reduction of 5-membered ring oxocarbenium ions to access highly substituted tetrahydrofurans.