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Regio‐ and Enantioselective Iridium‐Catalyzed N‐Allylation of Indoles and Related Azoles with Racemic Branched Alkyl‐Substituted Allylic Acetates
Author(s) -
Kim Seung Wook,
Schempp Tabitha T.,
Zbieg Jason R.,
Stivala Craig E.,
Krische Michael J.
Publication year - 2019
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.201902799
Subject(s) - enantioselective synthesis , iridium , allylic rearrangement , alkyl , chemistry , catalysis , regioselectivity , enantiomer , organic chemistry
Cyclometallated π‐allyliridium C,O‐benzoates modified with ( S )‐tol‐BINAP, which are stable to air, water, and SiO 2 , catalyze highly enantioselective N‐allylations of indoles and related azoles. This reaction complements previously reported metal‐catalyzed indole allylations in that complete levels of N versus C3 and branched versus linear regioselectivity are observed.