Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update

Abstract

The aza-Friedel–Crafts reaction allows an efficient coupling of electron-rich aromatic systems with imines for the facile incorporation of aminoalkyl groups into the aromatic ring. This reaction has a great scope of forming aza-stereocenters which can be tuned by different asymmetric catalysts. This review assembles recent advances in asymmetric aza-Friedel–Crafts reactions mediated by organocatalysts. The mechanistic interpretation with the origin of stereoselectivity is also explained.

Catalytic Synthesis of Atropoisomers via Non‐Canonical Friedel‐Crafts Reactions

“…In contrast, Friedel-Crafts alkylation reactions connect the aryl moiety to an sp 3 -hybridized carbon of central chirality when unsymmetrical groups are attached (Scheme 1A). Given the importance of enantioselective carbon-carbon bond formation in asymmetric syn-thesis, asymmetric Friedel-Crafts reactions, [4][5][6][7][8][9][10][11] predominantly alkylation reactions, have received great attention in the past decades. Various chiral catalysts, including chiral Lewis acids, Brønsted acids, and enzymes have been devised to control the enantioselectivity, which also overcomes the disadvantage of the stoichiometric use of metal chlorides.…”