Chiral Brønsted acid-catalyzed asymmetric dearomative spirocyclization of alkynyl thioethers

The regioselective transformation of alkynes represents a highly efficient bond-forming strategy in organic synthesis. However, the enantiocontrol in the conversion of alkynes remains challenging, especially for the metal-free approach. Herein, we describe a chiral Brønsted acid-catalyzed enantiosel...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2023-12, Vol.25 (24), p.1638-1643
Main Authors: Fan, Xin-Yang, Li, Jia-Cheng, Zhou, Ji-Jia, Zhou, Bo, Ye, Long-Wu
Format: Article
Language:English
Subjects:
Alkynes
Asymmetry
Enantiomers
Green chemistry
Phenols
Thioethers
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Summary:The regioselective transformation of alkynes represents a highly efficient bond-forming strategy in organic synthesis. However, the enantiocontrol in the conversion of alkynes remains challenging, especially for the metal-free approach. Herein, we describe a chiral Brønsted acid-catalyzed enantioselective spirocyclization of alkynyl thioethers via dearomatization of phenols. This metal-free protocol leads to the green and atom-economical preparation of chiral spiro[4.5]decan-6-ones in good to excellent yields with high enantioselectivities. Importantly, this protocol represents the first metal-free example of the asymmetric transformation of alkynyl thioethers. A chiral Brønsted acid-catalyzed asymmetric dearomative spirocyclization of alkynyl thioethers has been developed, leading to the green and atom-economical preparation of chiral sprio[4.5]decan-6-ones in good yields with high enatioselectivities.
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc03222a