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Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfonesстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Дата последнего поиска статьи во внешних источниках: 17 июля 2019 г.
- Авторы: Reznikov Alexander N., Sibiryakova Anastasiya E., Baimuratov Marat R., Golovin Eugene V., Rybakov Victor B., Klimochkin Yuri N.
- Журнал: Beilstein J. Org. Chem. , 1289–1297
- Том: 15
- Год издания: 2019
- Первая страница: 1289
- Последняя страница: 1297
- DOI: 10.3762/bjoc.15.127
- Аннотация: Functionally substituted sulfones with stereogenic centers are valuable reagents in organic synthesis and key motifs in some bioactive compounds. The asymmetric Michael addition of β-ketosulfones to conjugated nitroalkenes in the presence of Ni(II) complexes with various chiral vicinal diamines was studied. This reaction provides convenient access to non-racemic 4-nitro-2-sulfonylbutan-1-ones with two stereocenters with high yield and excellent enantioselectivity (up to 99%). It has been established that the catalytic Michael reaction itself was carried out with high diastereoselectivity, but the Michael adducts may epimerize at the C-2 position at a significant rate. Conditions for the preparation of individual diastereomers were found.
- Добавил в систему: Рыбаков Виктор Борисович