Tetrahedron

Mechanism and scope of salen bifunctional catalysts in asymmetric aldehyde and α-ketoester alkylation

…, EF DiMauro, EM O'Brien, V Annamalai, MC Kozlowski

Index: Fennie, Michael W.; DiMauro, Erin F.; O'Brien, Erin M.; Annamalai, Venkatachalam; Kozlowski, Marisa C. Tetrahedron, 2005 , vol. 61, # 26 p. 6249 - 6265

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Citation Number: 59

Abstract

Metal complexes of C2-symmetric Lewis acid/Lewis base salen ligands provide bifunctional activation resulting in rapid rates in the enantioselective addition of diethylzinc to aldehydes (up to 92% ee). Further experiments probed the reactivity of the individual Lewis acid and Lewis base components of the catalyst and established that both moieties are essential for asymmetric catalysis. These catalysts are also effective in the asymmetric addition of ...