Synthesis of C5-Allylindoles through an Iridium-Catalyzed Asymmetric Allylic Substitution/Oxidation Reaction Sequence of N‑Alkyl Indolines

Iridium/Brønsted acid cooperative catalyzed asymmetric allylic substitution reactions at the C5 position of indolines have been reported for the first time. The highly efficient protocol allows rapid access to various C5-allylated products in good to high yields (48–97%) and enantioselectivities (82...

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Bibliographic Details
Published in:Organic letters 2021-05, Vol.23 (9), p.3426-3431
Main Authors: Lu, Jiamin, Xu, Ruigang, Zeng, Haixia, Zhong, Guofu, Wang, Meifang, Ni, Zhigang, Zeng, Xiaofei
Format: Article
Language:English
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Summary:Iridium/Brønsted acid cooperative catalyzed asymmetric allylic substitution reactions at the C5 position of indolines have been reported for the first time. The highly efficient protocol allows rapid access to various C5-allylated products in good to high yields (48–97%) and enantioselectivities (82% to >99% ee) with wide functional group tolerance. The transformations allow not only the formation of C5-allylindoline derivatives but also the synthesis of C5-allylindole analogues in good yields and excellent stereoselectivities via an allylation/oxidation reaction sequence.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00810