Chiral 2-(2-Diphenylphosphinophenyl)-oxazolines: Synthesis and Use in Pd-Catalyzed Asymmetric Allylic Alkylation

Abstract

The synthesis of 2-(2-diphenylphosphinophenyl)-oxazolines from o-fluoroben-zonitrile and (-)-norephedrine or (+)-endo-2-hydroxy-endo-3-aminobornane is described. The Pa-catalyzed alkylation of (E)-1,3-diphenylallyl acetate with the sodium salt of dimethylmalonate using these chiral ligands occurs with an 82–87% yield and 88–93% ee.

Keywords:

• η³-allylpalladium
• allylic alkylation
• asymmetry
• catalysis
• oxazolines

Acknowledgments

We are grateful to “Ministère de la Recherche et de la Technologie” and “Région Champagne-Ardenne” for PhD studentships to Benjamin Ganchegui and Carole Chevrin, respectively.