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(S)-2-[(N-arylamino)methyl]pyrrolidines-Based Phosphoramidite P,N-Ligand Library for Asymmetric Metal-Catalyzed Allylic Substitution and Conjugate 1,4-Additionстатья
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: 13 мая 2020 г.
- Авторы: Gavrilov K.N., Mikhel I.S., Chuchelkin I.V., Zheglov S.V., Gavrilov V.K., Birin K.P., Tafeenko V.A., Chernyshev V.V., Goulioukina N.S., Beletskaya I.P.
- Журнал: ChemistrySelect
- Том: 1
- Номер: 14
- Год издания: 2016
- Первая страница: 4173
- Последняя страница: 4186
- DOI: 10.1002/slct.201600964
- Аннотация: A library of easy-to-prepare and modular chiral P,N-phosphoramidites based on [1,1’-biaryl]-2,2’-diols and C1-symmetric 1,2-diamines has been designed and developed. The structures of the novel ligands have been elucidated by means of 2D-NMR and confirmed in the solid state by X-ray diffraction analysis. Stereoselectors of this type exhibited high enantioselectivities in Pd-catalyzed allylic substitution reactions of (E)-1,3-diphenylallyl acetate with NaSO2pTol (up to 91% ee), CH2(CO2Me)2 (up to 89% ee), (C3H7)2NH (up to 94% ee) and (EtO)2P(O)CH2NH2 as a novel nucleophile (up to 98% ee). Ee values of up to 88% and 72% have been obtained in the Pd-catalyzed desymmetrization of N,N’-ditosyl-meso-cyclopent-4-ene-1,3-diol biscarbamate and in the Cu-catalyzed 1,4-conjugate addition of diethylzinc to chalcone, respectively. The reactions of P,N-bidentate ligands with [Pd(Cod)Cl2] at molar ratios of L/M=1 and 2 have been studied using 1H, 13C, 13C-1H HSQC, 13C-1H HMBC, 1H-1H COSY, 1H-1H ROESY, DOSY and 31PNMR spectroscopy as well as HR ESI mass spectrometry.
- Добавил в систему: Гулюкина Наталия Сергеевна