Asymmetric Synthesis of 3‑Methyleneindolines via Rhodium(I)-Catalyzed Alkynylative Cyclization of N‑(o‑Alkynylaryl)imines

The first asymmetric synthesis of 3-methyleneindolines from alkynyl imines has been developed via a rhodium-catalyzed tandem process: regioselective alkynylation of the internal alkynes and subsequent intramolecular addition to the imines. The reaction proceeded with unconventional chemoselectivity...

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Bibliographic Details
Published in:Organic letters 2021-06, Vol.23 (12), p.4823-4827
Main Authors: Yuan, Shi-Yi, Yan, Qi-Qi, Wang, Dan, Dan, Ting-Ting, He, Long, He, Cheng-Yu, Chu, Wen-Dao, Liu, Quan-Zhong
Format: Article
Language:English
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Summary:The first asymmetric synthesis of 3-methyleneindolines from alkynyl imines has been developed via a rhodium-catalyzed tandem process: regioselective alkynylation of the internal alkynes and subsequent intramolecular addition to the imines. The reaction proceeded with unconventional chemoselectivity and provided 3-methyleneindolines with good yields (up to 82% yield) and high enantioselectivities (up to 97% ee). Moreover, this transformation also features mild reaction conditions, perfect atom economy, and a broad substrate scope.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01518