Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 23, Pages 6660-6664Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201701767
Keywords
allenylindoles; C-H activation; enantioselectivity; ketones; manganese catalysis
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Funding
- Alexander von Humboldt Foundation
- Fonds der Chemischen Industrie
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A Mn-I-catalyzed regioselective C-H allenylation is reported that allows a broad range of 2-allenylindoles to be synthesized regioselectively on a gram scale under simple conditions. Notably, a highly efficient chirality transfer was observed (up to 93% ee) in this transformation. This procedure was further found to allow, for the first time, the direct preparation of ketones by Mn-I-catalyzed C-H activation. Mechanistic investigations revealed that the precoordination of the oxygen atom to the manganese center as well as the congested tertiary carbon atom in the propargylic carbonates play a crucial role.
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