化工进展 ›› 2016, Vol. 35 ›› Issue (S2): 258-266.DOI: 10.16085/j.issn.1000-6613.2016.s2.043

• 生物与医药化工 • 上一篇    下一篇

有机催化β-酮酸酯不对称α-羟基化反应研究进展

孟庆伟, 赵静喃, 王亚坤, 李智, 廉明明, 宋汪泽   

  1. 大连理工大学制药科学与技术学院, 辽宁 大连 116024
  • 收稿日期:2016-09-26 出版日期:2016-12-31 发布日期:2016-12-22
  • 通讯作者: 孟庆伟,教授。E-mail:mengqw@dlut.edu.cn。

Review on enantioselective α-hydroxylation of β-keto esters

MENG Qingwei, ZHAO Jingnan, WANG Yakun, LI Zhi, LIAN Mingming, SONG Wangze   

  1. School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116024, Liaoning, China
  • Received:2016-09-26 Online:2016-12-31 Published:2016-12-22

摘要: 手性α-羟基β-酮酸酯是多种天然产物及医药产品的重要中间体,获得这一类结构单元最简单的方法是β-酮酸酯的直接不对称α羟基化,因此该反应在医药工业和精细化工领域具有重要的研究价值。本文针对小分子金鸡纳碱衍生物、二萜类生物碱、芳氧基氨基醇及手性相转移催化剂直接氧化β-酮酸酯不对称α-羟基化反应研究,该反应的催化机理被认为是氢键、π-π键等多种分子间力协同作用,同时还需要适当的位阻基团遮蔽以获得羟基化反应立体选择性。

关键词: β-酮酸酯, 不对称α-羟基化, 有机催化, 不对称催化

Abstract: The chiral α-hydroxy-β-dicarbonyl is a common structural motif in a variety of natural products and pharmaceuticals and the most convenient way to obtain chiral α-hydroxylation compounds is the direct asymmetric oxidation of 1,3-dicarbonyl compounds.Thus,research on enantioselective α-hydroxylation of β-keto esters possess great value.This paper makes a brief summary of cinchona alkaloid derivatives,diterpenoid alkaloid derivatives,S-timolol analogues and phase-transfer catalysts applied to direct enantioselective hydroxylation of β-keto ester compounds.The possible mechanism of these catalysts is believed to be the outcome of combined action of various intermolecular forces,namely hydrogen bonding,π-π stacking and electrovalent bonding.

Key words: β-keto esters, enantioselective α-hydroxylation, organocatalysts, asymmetric catalysis

中图分类号: 

京ICP备12046843号-2;京公网安备 11010102001994号
版权所有 © 《化工进展》编辑部
地址:北京市东城区青年湖南街13号 邮编:100011
电子信箱:hgjz@cip.com.cn
本系统由北京玛格泰克科技发展有限公司设计开发 技术支持:support@magtech.com.cn