Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans

Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans Full article

Journal

Organic Chemistry Frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129

Output data

Year: 2022, Volume: 9, Number: 3, Pages: 737-744 Pages count : 8 DOI: 10.1039/d1qo01646f

Authors

Fadeev Alexander A. ¹ , Makarov Anton S. ¹ , Ivanova Olga A. ² , Uchuskin Maxim G. ¹ , Trushkov Igor V. ^3,4

Affiliations

1	Department of Chemistry, Perm State University, Bukireva 15, Perm 614990, Russian Federation
2	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119991, Russian Federation
3	D. Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow 117997, Russian Federation
4	N. D. Zelinsky Institute of Organic Chemistry, Leninsky pr. 47, Moscow 119334, Russian Federation

We report the divergent synthesis of benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans using the concept of extended Corey–Chaykovsky reactions. With this concept, 2-hydroxychalcones were treated with the Corey ylide providing highly reactive donor–acceptor cyclopropanes that were introduced in a one pot manner for further transformations. We demonstrated that the nucleophilic three-membered ring opening followed by cyclization under mild reaction conditions afforded the 2,8-dioxabicyclo[3.2.1]octane scaffold. On the other hand, heating the intermediates with a strong Brønsted acid furnished 2-phenacyl-2,3-dihydrobenzofurans. These transformations, resulting in products with crucially different heterocyclic skeletons from the same starting compounds, demonstrate the enormous potential of the extended Corey–Chaykovsky reaction.

Fadeev A.A. , Makarov A.S. , Ivanova O.A. , Uchuskin M.G. , Trushkov I.V.
Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans
Organic Chemistry Frontiers. 2022. V.9. N3. P.737-744. DOI: 10.1039/d1qo01646f WOS Scopus OpenAlex

Web of science:	WOS:000732841800001
Scopus:	2-s2.0-85124553412
OpenAlex:	W4200460627

DB	Citing
OpenAlex	16
Scopus	15
Web of science	16