Synthesis of ferrocene-based amido-phosphine ligands via highly diastereoselective ortho-lithiation and their application in Pd-catalyzed asymmetric allylic alkylations

• DOI: 10.1016/j.tetasy.2011.06.014
• Publication Date: 2011-07-25T11:16:41Z
• Authors: Irena Philipova; Georgi Stavrakov; Angel Chimov; Rositsa Nikolova; Boris Shivachev; Vladimir Dimitrov
• Keywords: 01 natural sciences; 0104 chemical sciences

An efficient synthesis of novel planar chiral ferrocene-based amido-phosphine ligands was accomplished via highly diastereoselective ortho-lithiation and subsequent in situ trapping with chlorodiphenylphosphine. The palladium complexes of mono-phosphino ferrocenecarboxamide, bis-phosphino ferrocenedicarboxamide ligands, and analogues with a ferrocenophane framework were applied in the allylic alkylation of (E)-1,3-diphenyl-2-propenyl acetate. The reactions proceeded with excellent conversions and ee’s of up to 82%, the most efficient being the camphane based mono-phosphino ferrocenecarboxamide 2.