Regio- and Enantioselective Iridium-Catalyzed Amination of Alkyl-Substituted Allylic Acetates with Secondary Amines

Robust air-stable cyclometalated π-allyliridium C,O-benzoates modified by (S)-tol-BINAP catalyze the reaction of secondary aliphatic amines with racemic alkyl-substituted allylic acetates to furnish products of allylic amination with high levels of enantioselectivity. Complete branched regioselectiv...

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Bibliographic Details
Published in:Organic letters 2022-01, Vol.24 (1), p.441-445
Main Authors: Jung, Woo-Ok, Yoo, Minjin, Migliozzi, Madyson M, Zbieg, Jason R, Stivala, Craig E, Krische, Michael J
Format: Article
Language:English
Subjects:
Acetates - chemistry
Allyl Compounds - chemistry
Amination
Amines - chemistry
Catalysis
Iridium - chemistry
Molecular Structure
Stereoisomerism
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Summary:Robust air-stable cyclometalated π-allyliridium C,O-benzoates modified by (S)-tol-BINAP catalyze the reaction of secondary aliphatic amines with racemic alkyl-substituted allylic acetates to furnish products of allylic amination with high levels of enantioselectivity. Complete branched regioselectivities were observed despite the formation of more highly substituted C–N bonds.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c04135