有机化学 ›› 2001, Vol. 21 ›› Issue (11): 1074-1080. 上一篇    下一篇

研究论文

Sm(Ⅲ)催化的三级环氧醇高度非对映选择性重排还原 反应-1, 3-二醇单酯的新 合成方法

樊春安;宋振雷;涂永强;王保民   

  1. 兰州大学化学系应用有机化学国家重点实验室.甘肃
  • 发布日期:2001-11-25

Sm(Ⅲ)-catalyzed highly diastereoselective rearrangement and reduction of α-hydroxy epoxides-a new synthetic method for preparing 1, 3-diol monoesters

Fan Chunan;Song Zhenlei;Tu Yongqiang;Wang Baomin   

  1. Department of Chemistry, National Laboratory of Applied Organic. LActa Botanica Sini
  • Published:2001-11-25

本文报道了一个α-羟基环氧化物被Sm(Ⅲ)催化的新颖的串联反应。此反应一步完成了两个连续反应,高度非对映选择性地构筑了三个连续的立体中心。它可以成为一种高度非对映选择性地构筑2-季碳-1,3-二醇结构的一般方法。该反应的条件和机理在文中也作了详细的讨论。

关键词: 反应机理, 选择性, 二醇, 羟基, 环氧化物, 串联反应, 钐化合物, 碘化钐, 非对映立体异构, 合成法

A new Sm(Ⅲ)-catalyzed tandem reaction of α-hydroxy epoxide has been discovered, where two catalyti reactions occur sequentially in one-pot and afford three contiguous stereocenters in a highly diastereoselective manner. It could be developed to a general procedure for diastereoselective construction of 2-quaternary-1, 3- diol units. Extensive investigations of the reaction conditions and mechanism are also described.

Key words: REACTION MECHANISM, SELECTIVITY, HYDROXY GROUP, EPOXIDE, SAMARIUM COMPOUNDS, DIASTEROISOMERISM, SYNTHESIS METHODS

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