姜茹,匡永清,张生勇.Resin-OsO4-金鸡纳生物碱:一种在(E)-二苯乙烯不对称双羟化反应中可循环使用的高效催化剂[J].分子催化,2003,(6):405-408
Resin-OsO4-金鸡纳生物碱:一种在(E)-二苯乙烯不对称双羟化反应中可循环使用的高效催化剂
Resin-OsO4-Cinchona Alkaloid: A Highly Efficient and Recyclable Catalyst for Asymmetric Dihydroxylation for (E)-Stilbene
  修订日期:2003-05-26
DOI:
中文关键词:  Resin-OsO4催化剂 金鸡纳生物碱配体 不对称双羟化反应 手性连二醇 不对称合成
英文关键词:Resin-OsO_4 catalyst,Cinchona alkaloid ligands,Asymmetric dihydroxylation,Chiral vicinal diols,Asymmetric synthesis
基金项目:国家自然科学基金课题(29972055, 20002008).
姜茹  匡永清  张生勇
姜茹(第四军医大学基础部,化学教研室,陕西,西安,710032)
;匡永清(第四军医大学基础部,化学教研室,陕西,西安,710032)
;张生勇(第四军医大学基础部,化学教研室,陕西,西安,710032)
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中文摘要:
      用改进的方法把季铵盐共价结合在Merrifield树脂上作为离子交换剂与K2O5O4作用制成Resin—OsO4催化剂,在NaH存在下,以DMF作溶剂,在70℃下奎宁或奎尼丁与1,4-二氯二氮杂萘反应高产率地生成(QN)2PHAL或(QD)2PHAL,Resin—OsO4通过简单过滤可定量回收,回收的催化剂重复使用五次,其活性不变,Resin—OsO4-(QN)2PHAL或(QD)2PHAL催化体系在(E)-二苯乙烯的不对称双羟化反应中的化学产率为84~91%,立体选择性为96-99%ee。
英文摘要:
      Resin-OsO_4 catalyst was prepared by an improved procedure using quaternary ammonium salts covalently bound to Merrifield resin as ion-exchanger. Two bis-cinchona alkaloid ligands were synthesized in high yield by treating 1, 4-dichlorophtalazine with quinine or quinidine in the presence of NaH in DMF. Application of Resin-OsO_4-(QN)_2PHAL or (QD)_2PHAL to the asymmetric dihydroxylation of trans-stilbene afforded corresponding chiral diols in 84%~91% yields and 96%~99% ees. The Resin-OsO_4 was recovered quatitavely by a simphe filtration and reused for 5 cycles with consistent activity.
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