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用于烯烃二羟化反应的一种经济,高效且可重复使用的催化体系
引用本文:金瑛,孙晓莉,姜茹,张生勇.用于烯烃二羟化反应的一种经济,高效且可重复使用的催化体系[J].中国化学,2005,23(3):326-329.
作者姓名:金瑛  孙晓莉  姜茹  张生勇
作者单位:第四军医大学化学教研室,西安 710032
摘    要:以价廉的3,6-二氯哒嗪和奎宁为原料,通过两步反应即可得到一种可重复使用的金鸡纳生物碱衍生物配体。以NMO为辅助氧化剂在丙酮-水体系中,将此配体用于七种烯烃的不对称二羟化反应。反应结束后,用乙醚将产品从催化体系中萃取出来,得到80%~93%的产率和51%~99%的对映体过量值。以反式-二苯乙烯为底物进行催化体系的重复使用试验。循环使用十次,得到88%~92%的产率和>99%的对映体过量值。

关 键 词:催化剂  石蜡  二羟基化  奎宁  生物碱  配合基体
收稿时间:2004-2-9
修稿时间:2004-11-15

An Economical,Highly Efficient and Recyclable Catalyst System for Asymmetric Dihydroxylation of Olefins
Jin Ying,Sun Xiao‐Li,Jiang Ru,Zhang Sheng‐Yong.An Economical,Highly Efficient and Recyclable Catalyst System for Asymmetric Dihydroxylation of Olefins[J].Chinese Journal of Chemistry,2005,23(3):326-329.
Authors:Jin Ying  Sun Xiao‐Li  Jiang Ru  Zhang Sheng‐Yong
Abstract:A reusable cinchona alkaloid derivative ligand, which could be easily synthesized by two step transformation with cheap 3,6‐dichloropyridazine and quinine as materials, was applied to homogeneous asymmetric dihydroxylation of olefins with NMO as co‐oxidant in Me2CO‐H2O system and the products could be extracted with Et2O from the recyclable catalyst system. 80%–93% yield and 51%–99% ee have been obtained. When trans‐stilbene was chosen as the substrate for recycling experiment, 88%–92% yield and > 99% ee have been obtained for ten recycles.
Keywords:cinchona alkaloid derivative ligand  asymmetric dihydroxylation  recycle  chiral vicinal diol
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