Straightforward chemo- and stereoselective fluorocyclopropanation of allylic alcohols: exploiting the electrophilic nature of the not so elusive fluoroiodomethyllithium. Issue 58 (1st July 2019)

• Record Type: Journal Article
• Authors: Colella, Marco; Tota, Arianna; Großjohann, Angela; Carlucci, Claudia; Aramini, Andrea; Sheikh, Nadeem S.; Degennaro, Leonardo; Luisi, Renzo
• Is Part Of: Chemical communications. Volume 55:Issue 58(2019)
• Page Start: 8430
• Page End: 8433
• Publication Date: 2019-07-01
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc03394g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The not so elusive carbenoid fluoroiodomethyllithium disclosed its electrophilic nature in an unprecedented direct and stereoselective fluorocyclopropanation of allylic alcohols. Abstract : An unprecedented direct fluorocyclopropanation of allylic alcohols is reported. This simple method involves the not so elusive fluoroiodomethyllithium, a carbenoidic intermediate that under the developed conditions discloses its electrophilic nature. Gratifyingly, the reaction turned out to be highly chemo- and stereoselective, and DFT calculations provided insights into the structure and nature of this new type of carbenoid.