Exploring F/CF3 substituted oxocarbenium ions for the diastereoselective assembly of highly substituted tetrahydrofurans. Issue 27 (20th March 2023)

• Record Type: Journal Article
• Authors: Fernandes, Anthony J.; Michelet, Bastien; Panossian, Armen; Martin-Mingot, Agnès; Leroux, Frédéric R.; Thibaudeau, Sébastien
• Is Part Of: Chemical communications. Volume 59:Issue 27(2023)
• Page Start: 4083
• Page End: 4086
• Publication Date: 2023-03-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc06521e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : 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. 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.