Chiral P,S-bidentate diamidophosphites with 1,2-thioether alcohol-based exocyclic substituents in asymmetric Pd-catalyzed reactions

Chiral P*,S-diamidophosphites with a 1,3,2-diazaphospholidine core and exocyclic 1,2-hydroxyl-thioether fragments were prepared. These asymmetric inducers provided up to 86% ee in the Pd-catalyzed allylic substitution of (E)-1,3-diphenylallyl acetate with dimethyl malonate and pyrrolidine, and up to...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2022-06, Vol.197 (5-6), p.518-519
Main Authors: Firsin, I. D., Chuchelkin, I. V., Gavrilov, V. K., Trunina, V. M., Zimarev, V. S., Zheglov, S. V., Gavrilov, K. N., Goulioukina, N. S.
Format: Article
Language:English
Subjects:
1,2-thioether alcohols
Alkylation
Asymmetry
Chemical reactions
Chiral diamidophosphites
Palladium
Pd-catalyzed asymmetric allylic substitution
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Summary:Chiral P*,S-diamidophosphites with a 1,3,2-diazaphospholidine core and exocyclic 1,2-hydroxyl-thioether fragments were prepared. These asymmetric inducers provided up to 86% ee in the Pd-catalyzed allylic substitution of (E)-1,3-diphenylallyl acetate with dimethyl malonate and pyrrolidine, and up to 76% in the Pd-mediated allylic alkylation of cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426507.2021.1989691