Fluorinated Imines in Tandem and Cycloaddition Reactions

Abstract

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.

Access to phosphorus-containing cyclopenta[b]benzofuranols via a serendipitous cascade reaction promoted by a bifunctional phosphonium salt

“…The severity of these obstacles can be lessened by performing a consecutive series of intramolecular reactions in a welldefined reaction sequence known as domino, tandem, or cascade processes, which feature high modularity, and rapid generation of molecular skeletons such as carbo-or heterocycles. [8][9][10] Over the past decades, these types of reactions have successfully been merged in the field of organocatalysis with their advantages of high efficiencies and mild reaction conditions. 10,11 Of these reactions, organocatalytic cascade reactions exhibit distinct superiorities, allowing for facile preparation of architecturally complex molecules with perfect atom economy in a single step, often using inexpensive and abundant starting feedstocks.…”