高等学校化学学报

高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (7): 1216.

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1,4-双(9-O-奎宁)-2,3-二氮杂萘的合成及其在烯烃不对称二羟基化反应中的应用

孙晓莉, 匡永清, 南鹏娟, 张生勇   

  1. 第四军医大学化学教研室, 西安 710032
  • 收稿日期:2002-07-02 出版日期:2003-07-24 发布日期:2003-07-24
  • 通讯作者: 张生勇(1939年出生),男,教授,博士生导师,主要从事催化不对称反应的研究.E-mail:syzhang@fmmu.edu.cn E-mail:syzhang@fmmu.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:29972055,20002008)资助

Synthesis of 1,4-Bis(9-O-quininyl)phthalazine and Its Application as a Ligand to the Catalytic Asymmetric Dihydroxylation of Olefins

SUN Xiao-Li, KUANG Yong-Qing, NAN Peng-Juan, ZHANG Sheng-Yong   

  1. The Teaching and Research Section of Chemistry, the 4th Military Medical University, Xi′an 710032, China
  • Received:2002-07-02 Online:2003-07-24 Published:2003-07-24

PDF (PC)

被引次数

49

摘要：

通过改进的文献方法制备1,4-双(9-O-奎宁)-2,3-二氮杂萘[(QN)2PHAL].在碱性条件下,奎宁与1,4-二氯-2,3-二氮杂萘之间的亲核取代反应以72%的化学产率生成(QN)2PHAL.在4种烯烃的不对称二羟基化反应中,(QN)2PHAL表现出很高的对映选择性(83%～92%e.e.)和催化活性(产率83%～93%).

关键词: 1,4-双(9-O-奎宁)-2,3-二氮杂萘, 不对称二羟基化, 手性连二醇

Abstract:

An improved procedure for the preparation of 1,4-bis(9-O-quininyl) phthalazine[(QN)2PHAL] and the rudimentary application of (QN)2PHAL to the catalytic asymmetric dihydroxylation of olefins were described. (QN)2PHAL was synthesized in a good yield by the reaction of quinine with 1,4-dichlorophthalazine in the presence of K2CO3 and KOH in refluxing toluene. The asymmetric dihydroxylation of four olefins with (QN)2PHAL as the chiral ligand showed an excellent enantioselectivity and activity.

Key words: 1,4-Bis(9-O-quininyl)phthalazine, Asymmetric dihydroxylation, Chiral vicinal diol

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