Catalytic asymmetric Friedel-Crafts reaction is one of the most efficient methods for the construction of optically active aryl-or heteroaryl-containing compounds. Since Friedel and Crafts reported the first example in 1877, this reaction has attracted wide attention. In recent twenty years, asymmetric catalytic Friedel-Crafts reaction has been well studied in the presence of a number of chiral bifunctional organocatalysts (such as derivatives of cinchona alkaloids, chiral prolinol ethers, chiral phosphoric acids, chiral thiourea, etc.) and various metal and chiral ligand (chiral N,N'-dioxide, chiral bis(oxazoline), chiral Schiff base) complexes. In this paper, we summarize the recent progress in asymmetric Friedel-Crafts reactions of phenols, pyrroles, furans and thiophenes. Finally, the deficiencies as well as the perspective of the Friedel-Crafts reaction have been highlighted.
Contents
1 Introduction
2 Catalytic asymmetric Friedel-Crafts reactions of phenols
2.1 Imines as the electrophiles
2.2 1, 2-Diketones as the electrophiles
2.3 Nitroalkenes as the electrophiles
2.4 α, β-Unsaturated carbonyl compounds as the electrophiles
2.5 Others double bonds as the electrophiles
3 Catalytic asymmetric Friedel-Crafts reactions of pyrroles
3.1 Nitroalkenes as the electrophiles
3.2 α, β-Unsaturated carbonyl compounds as the electrophiles
3.3 Others
4 Catalytic asymmetric Friedel-Crafts reactions of furans and thiophenes
5 Conclusion