Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 5, Pages 2105-2109Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201914049
Keywords
asymmetric synthesis; axial chirality; cross-coupling; homogeneous catalysis; indoles
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Funding
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF) [20021-178846/1]
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We report herein the first examples of a palladium-catalyzed 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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