Organocatalyzed AFCA of Aromatic Hydrocarbons

Asymmetric organocatalysis deals with the realization of enantioselective transformations by means of small chiral organic molecules [14]. In this realm, chiral acid catalysis and chiral amino-catalysis represent two well-established research fields featuring a rich portfolio of applications in asymmetric C—C and C—X bond-forming processes and reductions. 

This work represents a landmark in the area of stereoselective metal-free (i.e., aminocatalysis) alkylation of benzenes based on Michael-type condensation via covalent catalyst-substrate interaction [22]. Subsequently, asymmetric acid catalysis based on hydrogen bond catalyst-substrate recognitions has found elegant applications in 1,4-conjugated additions and direct condensation of arenes with carbonyl compounds. The following sections will be organized based on the reactivity exploited in the arene functionalization. 

SCHEME 5.12 Reaction machinery of the asymmetric amino-catalyzed alkylation of benzenes. 

2 Asymmetric Organocatalyzed Condensation of Arenes with Carbonyl Compounds and Their Nitrogen Derivatives 

SCHEME 5.13 Asymmetric alkylation of phenols with carbonyl compounds in the presence of chiral Cinchona alkaloids (PH 9-phenanthryl). 

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