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Fluorinated Imines in Tandem and Cycloaddition Reactions
Jorge Escorihuela1, Santos Fustero1
1Departamento de Química Orgánica, Universitat de València, Avda. Vicente Andrés Estellés s/n, Burjassot 46100, València, Spain.
Chemical Record (New York, N.Y.)
|January 12, 2023
Summary
Fluorinated chiral imines, particularly Ellman's imines, are crucial building blocks for synthesizing diverse enantioenriched compounds. This research highlights asymmetric tandem reactions and cycloadditions utilizing these versatile fluorinated molecules.
Area of Science:
- Organic Chemistry
- Asymmetric Synthesis
- Fluorine Chemistry
Background:
- The field of fluorinated compounds has rapidly expanded due to their unique properties.
- Fluorinated chiral imines, especially Ellman's imines, are vital synthons for creating complex molecules.
- These imines enable the synthesis of enantioenriched carbocycles and heterocycles with significant biological and synthetic utility.
Purpose of the Study:
- To review significant advancements in asymmetric tandem reactions and cycloadditions over the past two decades.
- To showcase the application of fluorinated chiral N-sulfinyl imines and derivatives as starting materials.
- To highlight the role of these compounds in diversity-oriented synthesis and the creation of valuable chemical entities.
Main Methods:
- Asymmetric tandem reactions, including intramolecular aza-Michael reactions (IMAMR).
- Diversity-oriented synthesis (DOS) strategies.
- Cycloaddition reactions such as the Pauson-Khand reaction and [2+2+2]-cycloadditions.
- Metathesis reactions, often starting from enyne compounds.
- Utilization of p-tolylsulfinyl group as a chiral inducer.
Main Results:
- Demonstration of the utility of fluorinated chiral N-sulfinyl imines in various asymmetric transformations.
- Successful synthesis of complex enantioenriched carbocycles and heterocycles.
- Expansion of synthetic methodologies for creating molecular diversity.
- Significant contributions to the field of asymmetric catalysis and organofluorine chemistry.
Conclusions:
- Fluorinated chiral imines are powerful tools for asymmetric synthesis.
- The reviewed methodologies provide efficient routes to valuable enantioenriched compounds.
- Continued exploration of fluorinated imines promises further advancements in synthetic chemistry.
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