Modular and Chemoselective Strategy for the Direct Access to α‑Fluoroepoxides and Aziridines via the Addition of Fluoroiodomethyllithium to Carbonyl-Like Compounds

An expeditious, high-yielding synthesis of rare α-fluoroepoxides and α-fluoroaziridines through the addition of the unkown fluoroiodomethyllithium (LiCHIF)formed via deprotonation the commercially available fluoroiodomethane with a lithium amide baseto carbonyl-like compounds is documented. The ri...

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Bibliographic Details
Published in:Organic letters 2019-01, Vol.21 (2), p.584-588
Main Authors: Monticelli, Serena, Colella, Marco, Pillari, Veronica, Tota, Arianna, Langer, Thierry, Holzer, Wolfgang, Degennaro, Leonardo, Luisi, Renzo, Pace, Vittorio
Format: Article
Language:English
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Summary:An expeditious, high-yielding synthesis of rare α-fluoroepoxides and α-fluoroaziridines through the addition of the unkown fluoroiodomethyllithium (LiCHIF)formed via deprotonation the commercially available fluoroiodomethane with a lithium amide baseto carbonyl-like compounds is documented. The ring-closure reactions, leading to α-fluorinated three-membered heterocycles, rely on the diversely reactive C–I and C–F bonds. Excellent chemoselectivity was observed in the presence of highly sensitive functionalitiesaldehyde, ketone, nitrile, alkenewhich remained untouched during the homologation sequence.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b04001