By the same authors

From the same journal

From the same journal

Iridium Catalyzed Enantioselective Intermolecular Indole C2-Allylation

Research output: Contribution to journalArticlepeer-review

Full text download(s)

Published copy (DOI)

Author(s)

Department/unit(s)

Publication details

JournalAngewandte Chemie International Edition
DateAccepted/In press - 21 Feb 2020
DateE-pub ahead of print - 24 Feb 2020
DatePublished (current) - 4 May 2020
Issue number19
Volume59
Pages (from-to)7598-7604
Early online date24/02/20
Original languageEnglish

Abstract

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 π-π stacking interactions have been identified as major contributors to the C2-selectivity.

Bibliographical note

© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

Projects

Discover related content

Find related publications, people, projects, datasets and more using interactive charts.

View graph of relations