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

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 highl...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-07, Vol.55 (58), p.843-8433
Main Authors: Colella, Marco, Tota, Arianna, Grojohann, Angela, Carlucci, Claudia, Aramini, Andrea, Sheikh, Nadeem S, Degennaro, Leonardo, Luisi, Renzo
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Stereoselectivity
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Summary: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. The not so elusive carbenoid fluoroiodomethyllithium disclosed its electrophilic nature in an unprecedented direct and stereoselective fluorocyclopropanation of allylic alcohols.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc03394g