Co/Zn Bimetallic Catalysis Enables Enantioselective Alkynylation of Isatins and α‑Ketoesters Using Terminal Alkynes

We present herein a novel cobalt/zinc bimetallic catalysis system for the realization of an efficient and enantioselective alkynylation of isatins and α-ketoesters using terminal alkynes. By using a simple procedure with all commercially available catalysts, including cobalt bromide, a chiral bispho...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-06, Vol.88 (12), p.7755-7763
Main Authors: Huang, Rui-Zhi, Ma, Zhan-Cai, Huang, Yuan, Zhao, Yu
Format: Article
Language:English
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Summary:We present herein a novel cobalt/zinc bimetallic catalysis system for the realization of an efficient and enantioselective alkynylation of isatins and α-ketoesters using terminal alkynes. By using a simple procedure with all commercially available catalysts, including cobalt bromide, a chiral bisphosphine ligand, and zinc triflate, a range of synthetically useful tertiary propargylic alcohols are accessed with high yields and good enantioselectivities. Control reactions showed that this catalytic system proceeds through activation of the terminal alkyne by zinc triflate and a base, transmetalation from zinc to cobalt, and then the enantio-determining alkynylation of ketones.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01369