Efficient Synthesis of Polysubstituted Furans through a Base-Promoted Oxacyclization of (Z)-2-En-4-yn-1-ols


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Output type: Journal article

UM6P affiliated Publication?: Yes

Author list: Hrizi A., Thiery E., Romdhani-Younes M., Jacquemin J., Thibonnet J.

Publisher: Wiley: 12 months

Publication year: 2021

Journal: European Journal of Organic Chemistry (1434-193X)

Volume number: 16

Issue number: 27

ISSN: 1434-193X

eISSN: 1099-0690

URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85107596246&doi=10.1002%2fejoc.202100471&partnerID=40&md5=597e9e1ac83518143f93ed7df76cef9e

Languages: English (EN-GB)


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Abstract

An efficient base catalyzed oxacyclization of Z-enynols has been developed under transition metal-free reaction conditions, thus resulting in a variety of new di-, tri-, and tetra-substituted furans. This approach allowed us to obtain 32 new compounds. Furthermore, DFT calculations were realized to depict a relationship between the natural population analysis and experimental results with alkyl or aryl groups for the synthesis of 2-benzylfuran. A one-pot Sonogashira/oxacyclization approach offers a flexible, robust and efficient alternative to base catalyzed cyclization is also carried out. © 2021 Wiley-VCH GmbH


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Last updated on 2021-20-09 at 23:22