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Tandem 1,3-Dipolar Cycloaddition/Rearrangement of Nitronates with Cyclooctyne for the Diastereoselective Synthesis of Spiroaziridine Derivatives Научная публикация

Журнал Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052
Вых. Данные Год: 2026, Том: 28, Номер: 13, Страницы: 4061-4066 Страниц : 6 DOI: 10.1021/acs.orglett.6c00553
Авторы Maksakova Polina I. 1,2 , Malykhin Roman S. 2 , Lukoyanov Alexander A. 2 , Lesnikov Vladislav K. 2 , Tabolin Andrey A. 2
Организации
1 Higher Chemical College, D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq. 9, Moscow 125047, Russian Federation
2 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119334, Russian Federation

Реферат: The 1,3-dipolar cycloaddition of cyclic nitronates (5,6-dihydro-4H-1,2-oxazine N-oxides) with cyclooctyne affords oxazine-annulated spiroaziridine derivatives in mild conditions with high yields and diastereoselectivity via consecutive strain-promoted [3 + 2]-cycloaddition/ring contraction. Isoxazoline N-oxides and silyl nitronates also react smoothly, albeit with a lower diastereoselectivity. DFT calculations reveal key features, such as half-boat conformation of the oxazine ring during cycloaddition, and control of the stereoselectivity during ring contraction by an anomeric effect in the O–N–O moiety.
Библиографическая ссылка: Maksakova P.I. , Malykhin R.S. , Lukoyanov A.A. , Lesnikov V.K. , Tabolin A.A.
Tandem 1,3-Dipolar Cycloaddition/Rearrangement of Nitronates with Cyclooctyne for the Diastereoselective Synthesis of Spiroaziridine Derivatives
Organic Letters. 2026. V.28. N13. P.4061-4066. DOI: 10.1021/acs.orglett.6c00553 WOS Scopus OpenAlex
Даты:
Поступила в редакцию: 3 февр. 2026 г.
Принята к публикации: 19 мар. 2026 г.
Опубликована в печати: 23 мар. 2026 г.
Опубликована online: 3 апр. 2026 г.
Идентификаторы БД:
≡ Web of science: WOS:001722398800001
≡ Scopus: 2-s2.0-105034794746
≡ OpenAlex: W7140197872
Альметрики: