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. 2020 Mar 6;22(5):2049-2053.
doi: 10.1021/acs.orglett.0c00465. Epub 2020 Feb 19.

Nickel-Catalyzed Asymmetric Friedel-Crafts Propargylation of 3-Substituted Indoles with Propargylic Carbonates Bearing an Internal Alkyne Group

Yusuke Miyazaki  1 , Biao Zhou  1 , Hiroaki Tsuji  1 , Motoi Kawatsura  1
Affiliations

Nickel-Catalyzed Asymmetric Friedel-Crafts Propargylation of 3-Substituted Indoles with Propargylic Carbonates Bearing an Internal Alkyne Group

Yusuke Miyazaki et al. Org Lett. .

Abstract

The nickel-catalyzed highly enantioselective Friedel-Crafts propargylation of 3-substituted indoles with propargylic carbonates bearing an internal alkyne group was developed. A wide array of the propargylic carbonates as well as 3-substituted indoles can be applicable to the asymmetric nickel catalysis, providing the corresponding chiral C-3 propargylated indolenine derivatives bearing two vicinal chiral centers in up to 89% yield with up to >99% ee and 94:6 dr (24 examples).

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