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

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (03): 334-340. Previous Articles Next Articles

Review

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

(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, Ailing^a; Zhang, Jintang^b; WANG, Zhiyong^*,b

(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

Abstract

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

Cite this article

Hui, Ailing^a; Zhang, Jintang^b; WANG, Zhiyong^*,b. Progress in Asymmetric Alkyl Addition to Aldehydes and Ketones Promoted by Tartaric Acid Derivatives[J]. Chin. J. Org. Chem., 2009, 29(03): 334-340.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[2]	Junjie Zhang, Xuetao Xu. [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3297-3303.
[3]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[4]	Wenqian Wu, Chunxia Chen, Jinsong Peng, Zhanyu Li. Research Progress of Carbonyl α-Position Amination [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2743-2763.
[5]	Xuzheng Zhang, Fengli Yu, Bing Yuan, Congxia Xie, Shitao Yu. Phase Transfer Catalytic Oxidation of Cyclopentene to Glutaraldehyde by Vanadium Molybdenum Heteropolyacid Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1444-1451.
[6]	Yuliang Chen, Fengkai He, Siyun Wang, Dingcheng Jia, Yaqun Liu, Yiyong Huang. Kinetic Resolution of Aldehydes Bearing an All-Carbon Quaternary Stereocenter at the α-Position by the Antilla Allylboration [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4294-4302.
[7]	Peng Zhou, Weiming Zhu, Jiantao Zhang, Duoduo Xiao, Xiangfeng Guo, Weibing Liu. Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3939-3944.
[8]	Yuehua Zhang, Fei Nie, Lu Zhou, Xiaofeng Wang, Yuan Liu, Yanping Huo, Wencheng Chen, Zujin Zhao. Synthesis and Optoelectronic Studies of Thermally Activated Delayed Fluorescence Materials Based on Benzothiazolyl Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3876-3887.
[9]	Duoduo Xiao, Jiantao Zhang, Peng Zhou, Weibing Liu. Metal-Free α-C(sp³)—H Methylenation of Aryl Ketones to Form γ-Keto Sulfoxides with Dimethyl Sulfoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3900-3906.
[10]	Yunpeng Qi, Dengkai Lin, Liang-An Chen. Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3861-3875.
[11]	Cunwei Qian, Rong Han, Zhixing Shen, Qian Li, Xuanrong Chen. N-Iodosuccinimide (NIS) Promoted Synthesis of 3-Substituted Indole Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2496-2503.
[12]	Junjiao Wang, Yuyu Lv, Yongwei Shang, Zhenli Cui, Ke-Hu Wang, Danfeng Huang, Yulai Hu. Research Progress of Reactions Participated by α-Hydroxy Ketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2300-2321.
[13]	Fasheng Shi, Shengwen Wang, Huan Xu, Xingxing Lu, Xinling Yang, Tengda Sun, Changkai Wang, Xiaoming Zhang, Qing Yang, Yun Ling. Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2106-2116.
[14]	Fei Yuan, Yan Zhao, Qingsong Guo, Fudan Yin, Jinrong Lai, Beifang Nian, Ming Zhang, E Tang. Synthesis of 1-[1-(Amino)cyclopropyl]ketones by Tandem Reaction Involving Vinyl Selenium Salt [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1759-1769.
[15]	Wenjing Yi, Wei Sun, Xinquan Hu, Chao Liu, Liqun Jin. Recent Advance of Ketones Synthesis from Carboxylic Esters [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1626-1639.

酒石酸衍生物促进的醛酮不对称烷基加成反应研究进展

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

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments