Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 19, Pages 7598-7604Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202001956
Keywords
allylic substitution; DFT calculations; enantioselective synthesis; indole; iridium
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Funding
- EPSRC [EP/R013748/1] Funding Source: UKRI
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The enantioselective intermolecular C2-allylation of 3-substituted indoles is reported for the first time. This directing group-free approach relies on a chiral Ir-(P, olefin) complex and Mg(ClO4)(2) Lewis acid catalyst system to promote allylic substitution, providing the C2-allylated products in typically high yields (40-99 %) and enantioselectivities (83-99 % ee) with excellent regiocontrol. Experimental studies and DFT calculations suggest that the reaction proceeds via direct C2-allylation, rather than C3-allylation followed by in situ migration. Steric congestion at the indole-C3 position and improved pi-pi stacking interactions have been identified as major contributors to the C2-selectivity.
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