Recent Advances in the Catalytic Asymmetric Friedel-Crafts Reactions of Indoles

ACS Omega. 2022 Oct 3;7(40):35446-35485. doi: 10.1021/acsomega.2c05022. eCollection 2022 Oct 11.

ABSTRACT

Functionalized chiral indole derivatives are privileged and versatile organic frameworks encountered in numerous pharmaceutically active agents and biologically active natural products. The catalytic asymmetric Friedel-Crafts reaction of indoles, catalyzed by chiral metal complexes or chiral organocatalysts, is one of the most powerful and atom-economical approaches to access optically active indole derivatives. Consequently, a wide range of electrophilic partners including α,β-unsaturated ketones, esters, amides, imines, β,γ-unsaturated α-keto- and α-ketiminoesters, ketimines, nitroalkenes, and many others have been successfully employed to achieve a plethora of functionalized chiral indole moieties. In particular, strategies for C-H functionalization in the phenyl of indoles require incorporation of a directing or blocking group in the phenyl or azole ring of indole. The discovery of chiral catalysts which can control enantiodiscrimination has gained a great deal of attention in recent years. This review will provide an updated account on the application of the asymmetric Friedel-Crafts reaction of indoles in the synthesis of diverse chiral indole derivatives, covering the timeframe from 2011 to today.

PMID:36249392 | PMC:PMC9558610 | DOI:10.1021/acsomega.2c05022

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