КФУ. Карточка публикации. Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes.

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TANDEM DIHETERO-DIELS&NDASH;ALDER AND HUISGEN CYCLOADDITION REACTIONS. SYNTHESIS, CRYSTAL STRUCTURE AND HYDROLYSIS OF THE NOVEL CAGE PHOSPHORANES.

Форма представления

Статьи в зарубежных журналах и сборниках

Год публикации

2018

Язык

английский

Авторы, сотрудники КФУ

Баронова Тамара Александровна, автор

Ефимов Сергей Владимирович, автор

Клочков Владимир Васильевич, автор

Миронов Владимир Федорович, автор

Миронова Екатерина Владимировна, автор

Хасиятуллина Надежда Рустэмовна, автор

Другие авторы

Литвинов Игорь Анатольевич, автор

Мусин Рашид Загитович, автор

Файзуллин Роберт Рустемович, автор

Библиографическое описание на языке оригинала

Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes / N.R. Khasiyatullina, T.A. Baronova, E.V. Mironova, R.R. Fayzullin, I.A. Litvinov, S.V. Efimov, R.Z. Musin, V.V. Klochkov and V.F. Mironov // Org. Chem. Front. – 2018. – V. 5, no. 21. – P. 3113–3128. – DOI 10.1039/c8qo00915e

Аннотация

The reaction of 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole with hexafluoroacetone, ethyltrifluoropyruvate and chloral leads to the formation of cage phosphoranes possessing the 1-phospha-2,6,8-trioxabicyclo[3.2.1]octane framework whose structure was established by the XRD method and NMR spectroscopy. The process involves dihetero-Diels–Alder and Huisgen 1,3-dipolar cycloaddition reactions and is accompanied by the simultaneous formation of the P–C and C–C bonds. Despite the generation of three chiral carbon atoms, the stereoselectivity of the process exceeds 96%. Hydrolysis leads to the formation of functionalized aldols and phosphonates.

Ключевые слова

dihetero-Diels?Alder reaction, Huisgen cycloaddition reaction, cage phosphorane, 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole, hexafluoroacetone, ethyltrifluoropyruvate, chloral, aldol, phosphonate

Название журнала

Organic Chemistry Frontiers

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https://repository.kpfu.ru/?p_id=187075

Полная запись метаданных

Поле DC	Значение	Язык
dc.contributor.author	Баронова Тамара Александровна	ru_RU
dc.contributor.author	Ефимов Сергей Владимирович	ru_RU
dc.contributor.author	Клочков Владимир Васильевич	ru_RU
dc.contributor.author	Миронов Владимир Федорович	ru_RU
dc.contributor.author	Миронова Екатерина Владимировна	ru_RU
dc.contributor.author	Хасиятуллина Надежда Рустэмовна	ru_RU
dc.contributor.author	Литвинов Игорь Анатольевич	ru_RU
dc.contributor.author	Мусин Рашид Загитович	ru_RU
dc.contributor.author	Файзуллин Роберт Рустемович	ru_RU
dc.date.accessioned	2018-01-01T00:00:00Z	ru_RU
dc.date.available	2018-01-01T00:00:00Z	ru_RU
dc.date.issued	2018	ru_RU
dc.identifier.citation	Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes / N.R. Khasiyatullina, T.A. Baronova, E.V. Mironova, R.R. Fayzullin, I.A. Litvinov, S.V. Efimov, R.Z. Musin, V.V. Klochkov and V.F. Mironov // Org. Chem. Front. – 2018. – V. 5, no. 21. – P. 3113–3128. – DOI 10.1039/c8qo00915e	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/?p_id=187075	ru_RU
dc.description.abstract	Organic Chemistry Frontiers	ru_RU
dc.description.abstract	The reaction of 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole with hexafluoroacetone, ethyltrifluoropyruvate and chloral leads to the formation of cage phosphoranes possessing the 1-phospha-2,6,8-trioxabicyclo[3.2.1]octane framework whose structure was established by the XRD method and NMR spectroscopy. The process involves dihetero-Diels–Alder and Huisgen 1,3-dipolar cycloaddition reactions and is accompanied by the simultaneous formation of the P–C and C–C bonds. Despite the generation of three chiral carbon atoms, the stereoselectivity of the process exceeds 96%. Hydrolysis leads to the formation of functionalized aldols and phosphonates.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	dihetero-Diels?Alder reaction	ru_RU
dc.subject	Huisgen cycloaddition reaction	ru_RU
dc.subject	cage phosphorane	ru_RU
dc.subject	2-(1-phenylvinyloxy)benzo-1	ru_RU
dc.subject	3	ru_RU
dc.subject	2-dioxaphosphole	ru_RU
dc.subject	hexafluoroacetone	ru_RU
dc.subject	ethyltrifluoropyruvate	ru_RU
dc.subject	chloral	ru_RU
dc.subject	aldol	ru_RU
dc.subject	phosphonate	ru_RU
dc.title	Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes.	ru_RU
dc.type	Статьи в зарубежных журналах и сборниках	ru_RU