Diastereoselective Deprotonative Metalation of Sugar-Derived Ferrocene Esters Using Mixed Lithium-Cadmium Combinations

Aare Sreeshailam (1, 2) , Gandrath Dayaker (1, 2) , Floris Chevallier (1) , Thierry Roisnel (3) , Palakodety Radha Krishna (2) , Florence Mongin (1)

1 CPM - Chimie et Photonique Moléculaires
2 Organic Chemistry Division III
3 ISCR - Institut des Sciences Chimiques de Rennes

The ability of a mixed lithium-cadmium amide to deproto-metallate diastereoselectively several sugar-derived ferrocene esters was studied. The ferrocenecarboxylates generated from α-D-glucofuranoses gave the best results, as evidenced after subsequent trapping with iodine. Good chemical yields and diastereoselectivities up to 82 % in favor of the SP stereoisomer were obtained. The use of a different chiral group favored the formation of the RP stereoisomer, isolated in 34 % yield and 98 % diastereoselectivity.

Mots clés: Metalation; Chiral auxiliaries; Sandwich complexes; Lithium; Carbohydrates

Domaines: Chimie organique

Aare Sreeshailam, Gandrath Dayaker, Floris Chevallier, Thierry Roisnel, Palakodety Radha Krishna, et al.. Diastereoselective Deprotonative Metalation of Sugar-Derived Ferrocene Esters Using Mixed Lithium-Cadmium Combinations. European Journal of Organic Chemistry, 2011, pp.3715-3718. ⟨10.1002/ejoc.201100264⟩. ⟨hal-00736552⟩