Novel β-Aminoalcohols with Bulky Substitutents and the Application in Enantioselective Addition of Diethyl Zinc to Arylaldehydes

Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (8): 943-945. Previous Articles Next Articles

新的含大体积取代基的β-氨基醇配体的合成及在二乙基锌对芳香醛的不对称加成反应中的应用

达朝山, 辛卓群, 肖亦男, 王恒山, 粟武, 杨帆, 王锐^*

兰州大学生命科学学院生物化学与分子生物学系兰州 730000

收稿日期:2003-09-24 修回日期:2003-12-19 接受日期:2004-02-20 发布日期:2022-09-20
通讯作者: * E-mail: wangrui@lzu.edu.cn
基金资助:
国家自然科学基金(No. 29972016)和甘肃省自然科学基金中青年基金(No. YS021-A23-008)资助项目.

Novel β-Aminoalcohols with Bulky Substitutents and the Application in Enantioselective Addition of Diethyl Zinc to Arylaldehydes

DA Chao-Shan, XIN Zhuo-Qun, XIAO Yi-Nan, WANG Heng-Shan, SU Wu, YANG Fan, WANG Rui^*

Department of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000

Received:2003-09-24 Revised:2003-12-19 Accepted:2004-02-20 Published:2022-09-20

Abstract

Two β-aminoalcohols possessingbulky substituents on the carbon atom with the hydroxyl group were readily synthesized from L-proline, and used as chiral ligands for catalytic asymmetricaddition of diethyl zinc to arylaldehydes. The resultant second alcohols withS configuration as well as good to higher ee values were achieved. The results showed that much bulkier substituents could not induce higher enantioselectivity.

Key words: β-aminoalcohol, asymmetric addition, carbonyl compound, chiral alcohol

Cite this article

DA Chao-Shan, XIN Zhuo-Qun, XIAO Yi-Nan, WANG Heng-Shan, SU Wu, YANG Fan, WANG Rui. Novel β-Aminoalcohols with Bulky Substitutents and the Application in Enantioselective Addition of Diethyl Zinc to Arylaldehydes[J]. Chinese Journal of Organic Chemistry, 2004, 24(8): 943-945.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

1 Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757 and references cited therein.
2 Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
3 Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc.1987, 109, 7111.
4 Da, C. S.; Han, Z. J.; Ni, M.; Yang, F.; Liu, D. X.; Zhou, Y. F.; Wang, R. Tetrahedron: Asymmetry 2003, 14, 659.
5 Yang, X. W.; Shen, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Liu, D. X.; Wang, R.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett.2001, 42, 3511.
6 Anderson, J. C.; Harding, M. Chem. Commun. 1998,393.
7 Anderson, J. C.; Cubbon, R.; Harding, M.; James, D. S. Tetrahedron: Asymmetry 1998, 9, 3461.
8 Pritchet, S.; Woodmansee, D. H.; Gantzel, P.; Walsh, P. J. J.Am. Chem. Soc. 1998, 120, 6432.
9 Liu, D. X.; Zhang, L. C.; Wang, Q.; Da, C. S.; Xin, Z. Q.; Wang,R.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2001, 3, 2733.
10 Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
11 Pastor, I. M.; Adolfsson, H. Tetrahedron Lett. 2002, 43, 1743.
12 Zhang, W.; Yoshinaga, H.; Imai, Y.; Kida, T.; Nakatsuji, Y.; Ikeda, I.Synlett 2000, 1512.
13 Yang, X. W.; Shen, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295.
14 Sellner, H.; Faber, C.; Rheiner, D. B.; Seebach, D. Chem. Eur. J.2000, 6, 3692.
15 Sato, I.; Kodaka, R.; Hosoi, K.; Soai, K. Tetrahedron: Asymmetry 2002, 13, 805.
16 Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970.
17 Yang, X. W.; Shen, J. H.; Da, C. S.; Wang, R.; Choi, M. C. K.; Yang, L.W.; Wong, K. Y. Tetrahedron: Asymmetry 1999, 10, 133.
18 Enders, D.; Kipphandt, H.; Gendes, P.; Brena-Valle, L. J.; Vhushan, V.Bull. Soc. Chim. Belg. 1988, 97, 691.
19 Yang, X. W.; Ni, J. M.; Wang, R.; Pan, X. F. Chem. J. Chin. Univ.1997, 18, 911 (in Chinese).
(杨晓武, 倪京满, 王锐, 潘鑫复, 高等学校化学学报, 1997, 18, 911.)
20 We have also prepared L-prolinol directly via reduction of L-proline with LiAlH₄ and used it as chiral ligand to catalyze the asymmetric addition of diethylzinc to benzaldehyde. However, the simple chiral β-aminoalcohol only gave 4% ee value.
21 Nugent, W. A. Org. Lett. 2002, 4,2133.

[1]	Junjie Zhang, Xuetao Xu. [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3297-3303.
[2]	Min Xi, Chao Duan, Jie Chi, Tian Fu, Xiaolong Su, Hongshe Wang. An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3312-3318.
[3]	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.
[4]	Zhihao Chen, Qi Fan, Biaolin Yin, Qingjiang Li, Honggen Wang. Progress in the Syntheses of α-Boryl Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1706-1712.
[5]	Weidi Cao, Xiaohua Liu. Recent Advances on Catalytic Enantioselective Protonation for Construction of α-Tertiary Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 961-973.
[6]	Jiantao Zhang, Yawen Deng, Nuolin Mo, Lianfen Chen. Advances in Radical Mediated 1,2-Aryl Migration Reactions of α,α-Diarylallyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 426-435.
[7]	Feixue Xue, Jianwei Zeng, Taishan Yan, Jie Han, Zhengjie He. Synthesis of Polysubstituted 2,3-Dihydrofurans via P(NMe₂)₃- Mediated [1＋4] Annulation of 1,2-Dicarbonyl Compounds with α,β-Unsaturated Ketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3805-3815.
[8]	Zhupeng Gao, Kai Xiang, Xuetao Xu, Yating Zhang, Daoyong Zhu. α-Benzoyloxylation of β-Dicarbonyl Compounds Involving Cyclic Trivalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3766-3775.
[9]	Binyang Jiang, Shi-Liang Shi. Recent Progress in Upgrading of Alcohol and Amine via Asymmetric Dehydrogenative Coupling [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3263-3279.
[10]	Wenxin Zhao, Mengjun Huang, Shengnan Li, Yujing Liu, Zhongqiu Liu, An'guo Ying. One-Pot Synthesis of 3,4-Dihydropyrimidine-2-one Derivatives via Biginelli Reactions Catalyzed by SnCl₂@MNPs [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2743-2749.
[11]	Wan Wan, Jibing Liu, Xueliang Huang. Gold-Catalyzed Selective Oxidation of 1,3-Diynamides to Access 4-Oxo-but-2-ynamides [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 376-383.
[12]	Quan Jining, He Xiaoxue, Yan Xinhuan, Li Xiaoqing, Xu Xiangsheng. Synthesis of 5-Iodomethyl Dihydrofurans via t-Butyl Hydroperoxide-Induced Lodocyclization of Olefinic Dicarbonyl Compounds with I₂ [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 1033-1037.
[13]	Zhu Dong-Xing, Xu Ming-Hua. Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 255-275.
[14]	Sun Guijiu, Xiao Fanhua, Duan Weiliang. Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to Quinone Monoketals [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 61-68.
[15]	Yang Shengbiao, Li Yan, Zhang Qian. Copper-Catalyzed Cyclization of 1-Aryl-1-cycloalcohols and 1,3-Dicarbonyl Compounds: Synthesis of Cycloalkane-Fused Dihydrofuran Derivatives [J]. Chinese Journal of Organic Chemistry, 2019, 39(8): 2226-2234.

新的含大体积取代基的β-氨基醇配体的合成及在二乙基锌对芳香醛的不对称加成反应中的应用

Novel β-Aminoalcohols with Bulky Substitutents and the Application in Enantioselective Addition of Diethyl Zinc to Arylaldehydes

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments