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

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

Marco Colella, Arianna Tota, Angela Grossjohann, Claudia Carlucci, Andrea Aramini, Nadeem S. Sheikh, Leonardo Degennaro and Renzo Luisi
Chemical communications (Cambridge, England), Vol.55(58), pp.8430-8433
25/07/2019
DOI: https://doi.org/10.1039/c9cc03394g
PMID: 31259351

Abstract

Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology
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.

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