Fluorinated Imines in Tandem and Cycloaddition Reactions

The chemistry of fluorinated compounds has experienced extraordinary growth in recent decades due to the many and varied properties which many of the compounds that contain fluorinated groups possess. Among all of them, fluorinated chiral imines, in particular the Ellman's imines, are of great importance since they are some of the most interesting building blocks for the synthesis of a large number of enantioenriched carbocycles and heterocycles with extraordinary biological and synthetic properties. This personal account covers the most significant results obtained in our research group in the last two decades concerning asymmetric tandem reactions, paying special attention to the intramolecular aza-Michael reaction (IMAMR), diversity oriented synthesis (DOS), asymmetric tandem reactions involving a p-tolylsulfinyl group as chiral inducer and cycloaddition processes, in particular, the Pauson-Khand reaction, [2+2+2]-cycloadditions and metathesis reactions, starting mainly from enyne compounds and through the use of fluorinated chiral N-sulfinyl imines and their derivatives as starting materials.

Automated summary

The chemistry of fluorinated compounds has grown significantly in recent decades due to the diverse properties they possess. Among them, fluorinated chiral imines, especially the Ellman's imines, are crucial in the synthesis of enantioenriched carbocycles and heterocycles with exceptional biological and synthetic properties. This personal account highlights the important findings of our research group in the past two decades, focusing on asymmetric tandem reactions, particularly the intramolecular aza-Michael reaction, diversity oriented synthesis, asymmetric tandem reactions involving a p-tolylsulfinyl group, cycloaddition processes, and the use of fluorinated chiral N-sulfinyl imines and their derivatives as starting materials for enyne compounds in Pauson-Khand reactions, [2+2+2]-cycloadditions, and metathesis reactions.