2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination
2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination
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DOI：
10.1016/j.tetasy.2009.02.050
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发表时间：
2009-05-25
影响因子：
--
通讯作者：
Coe, Diane
中科院分区：
文献类型：
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作者：
Assalit, Aurelie;Billard, Thierry;Coe, Diane
以2，2 ′-联吡啶-3，3 ′-二羧酸为原料合成了10个新的碳水化合物取代的联吡啶化合物。作为其作为手性配体的初步探索，Cu（II）催化的模型β-酮酯的不对称亲电取代使用这些简单和容易获得的手性联吡啶进行了研究。在该反应中仅观察到适度的对映选择性，尽管ee在与已知的和更精细的配体提供的那些相似的范围内。(C)2009爱思唯尔有限公司保留所有权利。
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 beta-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands. (C) 2009 Elsevier Ltd. All rights reserved.