Application of mixed phosphorus/sulfur ligands based on terpenoids in Pd-catalyzed asymmetric allylic substitution and Rh-catalyzed hydrogenation

Gavrilov, K.N.; Chuchelkin, I.V.; Gavrilov, V.K.; Firsin, I.D.; Trunina, V.M.; Shiryaev, A.A.; Shkirdova, A.O.; Bermesheva, E.V.; Tafeenko, V.A.; Chernyshev, V.V.; Zimarev, V.S.; Goulioukina, N.S.

Статья опубликована в высокорейтинговом журнале

Информация о цитировании статьи получена из Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 18 сентября 2024 г.

Авторы: Gavrilov Konstantin N., Chuchelkin Ilya V., Gavrilov Vladislav K., Firsin Ilya D., Trunina Valeria M., Shiryaev Alexey A., Shkirdova Alena O., Bermesheva Evgeniya V., Tafeenko Victor A., Chernyshev Vladimir V., Zimarev Vladislav S., Goulioukina Nataliya S.
Журнал: Organic and Biomolecular Chemistry
Том: 22
Номер: 31
Год издания: 2024
Издательство: Royal Society of Chemistry
Местоположение издательства: United Kingdom
Первая страница: 6362
Последняя страница: 6369
DOI: 10.1039/d4ob00840e
Аннотация: A small library of easily prepared diamidophosphite-sulfides based on 1,3-thioether alcohols, primarily of terpenoid nature, was developed. Upon complexation with Pd(II) ions, these hemilabile ligands showed the ability to form both P,S-chelates and complexes with two ligands P-monodentately bonded to the metal. The structures of the ligands and their complexes were determined by 2D NMR spectroscopy and X-ray diffraction. The use of these stereoselectors provided up to 95% ee in the classic Pd-catalyzed asymmetric allylic substitution reactions of (E)-1,3-diphenylallyl acetate with C- and N-nucleophiles and up to 80% ee in the Pd-mediated allylic alkylation of cinnamyl acetate with β-ketoesters. In addition, ee values of up to 90% with quantitative conversion were achieved in the Rh-catalyzed asymmetric hydrogenation of methyl esters of unsaturated acids. The effects of the structural parameters, reaction conditions and ligand-to-metal ratio on the catalytic results are discussed.
Добавил в систему: Чернышев Владимир Васильевич

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Application of mixed phosphorus/sulfur ligands based on terpenoids in Pd-catalyzed asymmetric allylic substitution and Rh-catalyzed hydrogenationстатья

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