2, 2′-Bipyridine-3, 3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu (II)-catalysed enantioselective …

…, T Billard, S Chambert, BR Langlois, Y Queneau…

Index: Assalit, Aurelie; Billard, Thierry; Chambert, Stephane; Langlois, Bernard R.; Queneau, Yves; Coe, Diane Tetrahedron Asymmetry, 2009 , vol. 20, # 5 p. 593 - 601

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Citation Number: 20

Abstract

A series of 10 new carbohydrate-substituted bipyridines were prepared from 2, 2′- bipyridine-3, 3′-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu (II)-catalysed asymmetric electrophilic fluorination of model β-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this ...

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