Mroczek, Agnieszka and Erre, Giulia and Taras, Rossana and Gladiali, Serafino Gabriele (2010) Chiral ferrocenyl ligands with bidentate pyridine donors. Synthesis and application in Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenylpropenyl-1-esters. Tetrahedron: Asymmetry, Vol. 21 (15), p. 1921-1927. eISSN 1362-511X. Article.
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A synthetic procedure relying on the Friedländer condensation of enantiopure α-amino ferrocenecarboxaldeyde has been devised for the regio-designed elaboration of a pyridine nucleus fused onto the ferrocene scaffold. Three novel bidentate ligands with different pyridine nitrogen donors featuring the [3,2-b]ferrocenopyridine fragment a as the sole chirogenic element have been prepared in enantiopure form through a multi step route involving the diastereoselective deprotonation of a chiral acetal of ferrocenecarboxaldehyde in the stereodetermining step. The ligands were assessed in the Pd-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl esters with good stereoselectivity.
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