Regio‐ and Enantioselective Iridium‐Catalyzed N‐Allylation of Indoles and Related Azoles with Racemic Branched Alkyl‐Substituted Allylic Acetates | Zendy

Kim Seung Wook | Zendy; Schempp Tabitha T. | Zendy; Zbieg Jason R. | Zendy; Stivala Craig E. | Zendy; Krische Michael J. | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201902799

Subject(s) - enantioselective synthesis , regioselectivity , chemistry , allylic rearrangement , iridium , catalysis , indole test , alkyl , stereoselectivity , organic chemistry , medicinal chemistry , stereochemistry

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.

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