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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (03): 334-340. 上一篇    下一篇

综述与进展

酒石酸衍生物促进的醛酮不对称烷基加成反应研究进展

惠爱玲a; 张金堂b ; 汪志勇*,b   

  1. (a合肥工业大学 农产品生物化工教育部工程研究中心 合肥 230009)
    (b中国科学技术大学化学系 合肥 230026)
  • 收稿日期:2008-03-26 修回日期:2008-07-19 发布日期:2009-03-20
  • 通讯作者: 汪志勇

Progress in Asymmetric Alkyl Addition to Aldehydes and Ketones Promoted by Tartaric Acid Derivatives

Hui, Ailinga ; Zhang, Jintangb; WANG, Zhiyong*,b   

  1. (a Engineering Research Center of Bio-process, Ministry of Education, Hefei University of Technology, Hefei 230009)
    (b Department of Chemistry, University of Science & Technology of China, Hefei 230026)
  • Received:2008-03-26 Revised:2008-07-19 Published:2009-03-20
  • Contact: WANG, Zhiyong

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被引次数

8 | 2

酒石酸分子具有含两个手性碳原子的对称结构, 且价廉易得. 因此, 酒石酸及其衍生物在不对称合成领域被广泛应用, 其中α,α,α’,α’-四苯基-2,2-二甲基-1,3-二氧环戊烷-4,5-二甲醇(简称TADDOL)及其类似物、手性酰氧硼烷(简称CAB)等促进的不对称催化反应研究得更为深入和细致. 综述了近年来TADDOL和CAB等作为手性配体在二乙基锌试剂与醛酮、烯丙基有机金属试剂以及烷基铈试剂与醛的加成反应中的应用, 同时简要地介绍了各手性配体的催化效果.

关键词: 烯丙基反应, 酒石酸, 二乙基锌, 不对称加成, 醛, 酮

Tartaric acid has the symmetrical structure with two chiral carbon atoms, which is cheap and available. As a result, tartaric acid and its derivatives are widely used in asymmetric synthesis, among which α,α,α’,α’-tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-bismethanol (TADDOL) and chiral (acyloxy)borane (CAB) have been studied detailedly in asymmetric catalysis. This paper will review the recent advances in application of TADDOL and CAB to asymmetric addition of diethylzinc to aldehydes or ketones, asymmet-ric addition of allylic organometallic reagents to aldehydes, asymmetric addition of alkyl cerium reagents to aldehydes. Also the catalytic effects are briefly discussed.

Key words: asymmetric addition, tartaric acid, allylation, aldehyde, diethylzinc, ketone