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Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

ABSTRACT: Cyclometallated ?-allyliridium C,O-benzoates modified with (S)-tol-BINAP, which are stable to air, water, and SiO2 , 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.

SUBMITTER: Kim SW

PROVIDER: S-EPMC6534432 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

Kim Seung Wook SW Schempp Tabitha T TT Zbieg Jason R JR Stivala Craig E CE Krische Michael J MJ

Angewandte Chemie (International ed. in English) 20190506 23

Cyclometallated π-allyliridium C,O-benzoates modified with (S)-tol-BINAP, which are stable to air, water, and SiO<sub>2</sub> , 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. ...[more]

PMID: 30964961

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