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

Abstract

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.

Graphical Abstract

Keywords:

• Chiral diamidophosphites
• 1,2-thioether alcohols
• Pd-catalyzed asymmetric allylic substitution

Additional information

Funding

This work was supported by the Russian Science Foundation (Project No. 19-13-00197).