Diverse “roof shape” chiral diamidophosphites: Palladium coordination and catalytic application

Gavrilov, K.; Chuchelkin, I.; Gavrilov, V.; Zheglov, S.; Firsin, I.; Trunina, V.; Zamilatskov, I.; Tyurin, V.S.; Tafeenko, V.; Chernyshev, V.V.; Zimarev, V.; Goulioukina, N.S.

Авторы: Gavrilov Konstantin, Chuchelkin Ilya, Gavrilov Vladislav, Zheglov Sergey, Firsin Ilya, Trunina Valeria, Zamilatskov Ilia, Tyurin Vladimir Sergeevich, Tafeenko Viktor, Chernyshev Vladimir V., Zimarev Vladislav, Goulioukina Nataliya Sergeevna
Журнал: New Journal of Chemistry
Том: 46
Номер: 4
Год издания: 2022
Издательство: Royal Society of Chemistry
Местоположение издательства: United Kingdom
Первая страница: 1751
Последняя страница: 1762
DOI: 10.1039/d1nj05143a
Аннотация: A series of diamidophosphite ligands of various structure and denticity were synthesized from (11S,12S)-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene as a “roof shape” 1,4-diol. On the basis of these ligands, we obtained three types of Pd(II) allylic complexes: a P,P-chelate, a P,S-bridged head-to-tail dinuclear complex, and сomplexes each containing a pair of P-monodentately coordinated P-, P,N- or P,S-ligands. The structures of the ligands and their complexes were determined by 2D NMR spectroscopy. Four diamidophosphites were additionally characterized by X-ray structural data. This kind of stereoselectors exhibited up to 98% ee in the Pd-mediated allylic substitution of (E)-1,3-diphenylallyl acetate with C- and N-nucleophiles. Ee values of up to 90% were obtained in the Pd-catalyzed allylic alkylation of cinnamyl acetate with various C-nucleophiles. In addition, up to 71% ee was achieved in the Pd-catalyzed asymmetric amination of 2-(diethoxyphosphoryl)-1-phenylallyl acetate with aniline, which is the pioneer example of diamidophosphite-type ligands involvement into this challenging reaction. The effects of the diamidophosphite moiety and the denticity of ligands on the catalytic activity and enantioselectivity were investigated.
Добавил в систему: Гулюкина Наталия Сергеевна

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Diverse “roof shape” chiral diamidophosphites: Palladium coordination and catalytic applicationстатья Исследовательская статья

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