Palladium-Catalyzed Enantioselective Cacchi Reaction: Asymmetric Synthesis of Axially Chiral 2,3-Disubstituted Indoles
We report herein the first examples of a palladiumcatalyzed enantioselective Cacchi reaction for the synthesis of indoles bearing a chiral C2-aryl axis. In the presence of a catalytic amount of Pd(OAc)2 and (R,R)-QuinoxP* ligand, reaction of N-aryl(alkyl)sulfonyl-2-alkynylanilides with arylboronic acids under oxygen atmosphere afforded enantioenriched 2,3-disubstituted indoles in high yields and enantioselectivity. The indole ring is constructed de novo in this process and a complexation-induced chirality transfer is proposed to account for the observed enantioselectivity.
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He, Y.-P., Wu, H., Wang, Q., & Zhu, J. (2020). Palladium-Catalyzed Enantioselective Cacchi Reaction: Asymmetric Synthesis of Axially Chiral 2,3-Disubstituted Indoles. Angewandte Chemie International Edition, 59(5), 2105–2109. https://doi.org/10.1002/anie.201914049
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2020
59
5
2105
2109
REVIEWED
EPFL