Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans
Тип публикации: Journal Article
Дата публикации: 2022-01-01
scimago Q1
wos Q1
БС1
SJR: 1.068
CiteScore: 8.2
Impact factor: 4.7
ISSN: 20524110, 20524129
Organic Chemistry
Краткое описание
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.
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Fadeev A. A. et al. 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. Vol. 9. No. 3. pp. 737-744.
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Fadeev A. A., Makarov A. S., Ivanova O., 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. Vol. 9. No. 3. pp. 737-744.
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TY - JOUR
DO - 10.1039/d1qo01646f
UR - https://xlink.rsc.org/?DOI=D1QO01646F
TI - Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans
T2 - Organic Chemistry Frontiers
AU - Fadeev, Alexander A
AU - Makarov, Anton S
AU - Ivanova, Olga
AU - Uchuskin, Maxim G
AU - Trushkov, Igor V
PY - 2022
DA - 2022/01/01
PB - Royal Society of Chemistry (RSC)
SP - 737-744
IS - 3
VL - 9
SN - 2052-4110
SN - 2052-4129
ER -
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@article{2022_Fadeev,
author = {Alexander A Fadeev and Anton S Makarov and Olga Ivanova and Maxim G Uchuskin and Igor V Trushkov},
title = {Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans},
journal = {Organic Chemistry Frontiers},
year = {2022},
volume = {9},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=D1QO01646F},
number = {3},
pages = {737--744},
doi = {10.1039/d1qo01646f}
}
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Fadeev, Alexander A., et al. “Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans.” Organic Chemistry Frontiers, vol. 9, no. 3, Jan. 2022, pp. 737-744. https://xlink.rsc.org/?DOI=D1QO01646F.