Palladium and rhodium-catalyzed enantioselective reactions mediated by pseudodipeptide-based phosphite-type ligand
- Authors: Gavrilov K.N.1, Chuchelkin I.V.1, Zheglov S.V.1, Gavrilov V.K.1, Novikov I.M.1, Firsin I.D.1, Shiryaev A.A.1
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Affiliations:
- S. A. Esenin Ryazan State University
- Issue: Vol 67, No 5 (2018)
- Pages: 916-922
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/242554
- DOI: https://doi.org/10.1007/s11172-018-2157-9
- ID: 242554
Cite item
Abstract
P*-Chiral diamidophosphite ligand of a 1,3,2-diazaphopholidine series bearing the exocyclic pseudodipeptide fragment was synthesized. The possibility of its application in the palladium- and rhodium-catalyzed asymmetric transformations was demonstrated. This ligand provided up to 84% ee in the Pd-catalyzed alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate, up to 56% ee in amination of this substrate with pyrrolidine, and up to 68% ee in alkylation of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate. In the Rh-catalyzed hydrogenation of (Z)-methyl 2-acetamido-3-phenylacrylate mediated by this ligand, up to 53% ee was achieved.
About the authors
K. N. Gavrilov
S. A. Esenin Ryazan State University
Author for correspondence.
Email: k.gavrilov@rsu.edu.ru
Russian Federation, 46 ul. Svobody, Ryazan, 390000
I. V. Chuchelkin
S. A. Esenin Ryazan State University
Email: k.gavrilov@rsu.edu.ru
Russian Federation, 46 ul. Svobody, Ryazan, 390000
S. V. Zheglov
S. A. Esenin Ryazan State University
Email: k.gavrilov@rsu.edu.ru
Russian Federation, 46 ul. Svobody, Ryazan, 390000
V. K. Gavrilov
S. A. Esenin Ryazan State University
Email: k.gavrilov@rsu.edu.ru
Russian Federation, 46 ul. Svobody, Ryazan, 390000
I. M. Novikov
S. A. Esenin Ryazan State University
Email: k.gavrilov@rsu.edu.ru
Russian Federation, 46 ul. Svobody, Ryazan, 390000
I. D. Firsin
S. A. Esenin Ryazan State University
Email: k.gavrilov@rsu.edu.ru
Russian Federation, 46 ul. Svobody, Ryazan, 390000
A. A. Shiryaev
S. A. Esenin Ryazan State University
Email: k.gavrilov@rsu.edu.ru
Russian Federation, 46 ul. Svobody, Ryazan, 390000