Premium
Manganese(I)‐Catalyzed Regioselective C−H Allenylation: Direct Access to 2‐Allenylindoles
Author(s) -
Lu Qingquan,
Greßies Steffen,
Klauck Felix J. R.,
Glorius Frank
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201701767
Subject(s) - regioselectivity , manganese , catalysis , chemistry , computer science , combinatorial chemistry , organic chemistry
Abstract 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.