Efficient Synthesis of Polysubstituted Furans through a Base‐Promoted Oxacyclization of (Z)‐2‐En‐4‐yn‐1‐ols. Issue 27 (7th June 2021)

• Record Type: Journal Article
• Authors: Hrizi, Asma; Thiery, Emilie; Romdhani‐Younes, Moufida; Jacquemin, Johan; Thibonnet, Jérôme
• Is Part Of: European journal of organic chemistry. Issue 27(2021)
• Page Start: 3798
• Page End: 3806
• Publication Date: 2021-06-07
• Subjects: Alkynols -- 5-Exo-dig oxacyclization -- Polysubstituted furans -- Tandem coupling/oxacyclization -- Transition-metal-free; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100471
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : An approach for the preparation of polysustituted furans through a metal‐free base‐catalyzed oxacyclization of (Z)‐2‐en‐4‐yn‐1‐ols is described. With this approach 32 new compounds were obtained. Furthermore, natural population analysis by DFT calculations, highlighted experimental results with alkyl or aryl groups for the synthesis of 2‐benzylfuran.