Issue 58, 2019

Straightforward chemo- and stereoselective fluorocyclopropanation of allylic alcohols: exploiting the electrophilic nature of the not so elusive fluoroiodomethyllithium

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.

Graphical abstract: Straightforward chemo- and stereoselective fluorocyclopropanation of allylic alcohols: exploiting the electrophilic nature of the not so elusive fluoroiodomethyllithium

Supplementary files

Article information

Article type
Communication
Submitted
02 মে 2019
Accepted
24 জুন 2019
First published
24 জুন 2019

Chem. Commun., 2019,55, 8430-8433

Straightforward chemo- and stereoselective fluorocyclopropanation of allylic alcohols: exploiting the electrophilic nature of the not so elusive fluoroiodomethyllithium

M. Colella, A. Tota, A. Großjohann, C. Carlucci, A. Aramini, N. S. Sheikh, L. Degennaro and R. Luisi, Chem. Commun., 2019, 55, 8430 DOI: 10.1039/C9CC03394G

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