Remote chirality transfer in nucleophilic catalysis with N-(4-pyridinyl)-L-proline derivatives
Remote chirality transfer in nucleophilic catalysis with N-(4-pyridinyl)-L-proline derivatives
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DOI：
10.1002/chir.10166
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发表时间：
2003-01-01
期刊：
影响因子：
2
通讯作者：
Fuji, K
中科院分区：
文献类型：
--
作者：
Kawabata, T;Stragies, R;Fuji, K
以L-脯氨酸为原料，制备了手性亲核催化剂5-15。在室温下，催化剂9和14促进了外消旋氨基醇衍生物16的酰化动力学拆分，选择性因子分别为8.1和11。由于这些催化剂中催化活性的吡啶环中不存在手性元素，手性从遥远的立体中心转移到反应中心(N-酰基吡啶)是造成对映体区别的原因。(C)2002年Wiley-Liss，Inc.
Chiral nucleophilic catalysts 5-15 were prepared starting from L-proline. Catalysts 9 and 14 promoted acylative kinetic resolution of racemic amino alcohol derivative 16 with selectivity factors of 8.1 and 11, respectively, at ambient temperature. Since chiral elements are not present in the catalytically active pyridine ring in these catalysts, chirality transfer from the remote stereogenic center to the reactive site (N-acylpyridinium) is suggested to be responsible for the differentiation between enantiomers. (C) 2002 Wiley-Liss, Inc.