Inducement of Poly[(S)-3-(4-vinylbenzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl] in the Asymmetric Addition of Diethylzinc toAromatic Aldehydes

doi:10.6023/cjoc201502011

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1797-1801.DOI: 10.6023/cjoc201502011 Previous Articles Next Articles

NOTE

聚[(S)-3-(4-乙烯基苄氧基)-2,2'-二羟基-1,1'-联萘]在二乙基锌和芳基醛的不对称加成反应中的诱导

刘大财, 朱维君, 张安林, 阳年发, 杨利文

湘潭大学化学学院环境友好化学与应用省部共建教育部重点实验室湘潭 411105

收稿日期:2015-02-07 修回日期:2015-03-16 发布日期:2015-04-13
通讯作者: 阳年发 E-mail:nfyang@xtu.edu.cn
基金资助:
国家自然科学基金(No. 21172186)和高等学校博士学科点专项科研基金(No. 20134301110004)资助项目.

Inducement of Poly[(S)-3-(4-vinylbenzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl] in the Asymmetric Addition of Diethylzinc toAromatic Aldehydes

Liu Dacai, Zhu Weijun, Zhang Anlin, Yang Nianfa, Yang Liwen

Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105

Received:2015-02-07 Revised:2015-03-16 Published:2015-04-13
Supported by:
Protect supported by the National Natural Science Foundation of China (No. 21172186) and the Higher Education Doctoral Science Foundation of China (No. 20134301110004).

1. Inducement of Poly[(S)-3-(4-vinylbenzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl] in the Asymmetric Addition of Diethylzinc toAromatic Aldehydes.PDF(3024KB)

Abstract

Poly[(S)-3-(4-vinylbenzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl] (poly-5a) was synthesized via radical polymerization and its asymmetric inducement in the addition of diethylzinc to aromatic aldehydes was studied. The addition products have good enantioselectivity with up to 89% enantiomeric excess (ee). Poly-5a can be easily recovered and reused without loss of catalytic activity.

Key words: radical polymerization, aromatic aldehyde, diethylzinc, asymmetric addition

Cite this article

Liu Dacai, Zhu Weijun, Zhang Anlin, Yang Nianfa, Yang Liwen. Inducement of Poly[(S)-3-(4-vinylbenzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl] in the Asymmetric Addition of Diethylzinc toAromatic Aldehydes[J]. Chin. J. Org. Chem., 2015, 35(8): 1797-1801.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J. I. Tetrahedron Lett. 1998, 39, 3783.
[2] Zhang, A. L.; Yu, Z. D.; Yang, N. F.; Yang, L. W. Tetrahedron: Asymmetry 2015, 26, 173.
[3] Rheiner, P. B.; Seebach, D. Chem. Eur. J. 1999, 5, 3221.
[4] Hu, Q. S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528.
[5] Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274.
[6] Arai, T.; Hu, Q. S.; Zheng, X. F.; Pu, L.; Sasai, H. Org. Lett. 2000, 2, 4261.
[7] Jayaprakash, D.; Sasai, H. Tetrahedron: Asymmetry 2001, 12, 2589.
[8] Zheng, L. S.; Song, T.; Xu, L. W. Chin. J. Org. Chem. 2014, 34, 1255 (in Chinese). (郑龙生, 宋涛, 徐利文, 有机化学, 2014, 34, 1255.)
[9] Harada, T.; Kanda, K. Org. Lett. 2006, 17, 3817.
[10] Emilio, F. M.; Beatriz, M.; Miguel, Y. Tetrahedron: Asymmetry 2012, 23, 789.
[11] Yusuke, M.; Toshiro, H. Angew. Chen. 2008, 120, 1104.
[12] Yu, H. B.; Zheng, X. F.; Lin, Z. M.; Hu, Q. S.; Huang, W. S.; Pu, L. J. Org. Chem. 1999, 64, 8149.
[13] Chen, R. F.; Qian, C. T. Tetrahedron 2001, 57, 9837.
[14] Wang, H. M.; Wang, Z.; Ding, K. L. Tetrahedron Lett. 2009, 50, 2200.
[15] Lin, Y. M.; Fu, I. P.; Uang, B. J. Tetrahedron: Asymmetry 2001, 12, 3217.
[16] Fu, I. P.; Uang, B. J. Tetrahedron: Asymmetry 2001, 12, 45.
[17] Yang, F.; Wei, S. P.; Chen, C. A.; Xi, P. H.; Yang, L.; Lan, J. B.; Gau, H. M.; You, J. S. Chem., Eur. J. 2008, 14, 2223.
[18] Zhao, J. B.; Wu, N. J.; Zhang, S.; Xi, P. H.; Su, X. Y.; Lan, J. B.; You, J. S. Angew. Chem., Int. Ed. 2009, 48, 8729.
[19] Dai, W. M.; Zhu, H. J.; Hao, X. J. Tetrahedron: Asymmetry 2000, 11, 2315.
[20] Gou, S. H.; Judeh, Z. M. A. Tetrahedron Lett. 2009, 50, 281.
[21] Yang, X. W.; Sheng, J. H.; Da, C. S.; Wang, H. S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295.
[22] Sokeirik, Y. S.; Omote, M.; Sato, K.; Kamadaki, I.; Ando, A. Tetrahedron: Asymmetry 2006, 17, 2654.
[23] Priego, J.; Mancheno, O. G.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346.
[24] Tanaka, T.; Yasuda, Y.; Hayashi, M. J. Org. Chem. 2006, 71, 7091.
[25] Cabrera, S.; Carretero, J. C. Chem. Commun. 2001, 2026.
[26] Manabu, H.; Takashi, M.; Kazuaki, I. J. Org. Chem. 2006, 71, 6474.
[27] Zhang, A. L.; Liu, Y. L.; Yang, N. F.; Yang, L. W. Tetrahedron: Asymmetry 2014, 24, 289.

聚[(S)-3-(4-乙烯基苄氧基)-2,2'-二羟基-1,1'-联萘]在二乙基锌和芳基醛的不对称加成反应中的诱导

Inducement of Poly[(S)-3-(4-vinylbenzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl] in the Asymmetric Addition of Diethylzinc toAromatic Aldehydes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Junjie Zhang, Xuetao Xu. [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3297-3303.
[2]	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.
[3]	Ren Xinfeng, Song Xiaoping, Ma Yingchao, Li Ya. Method for the Synthesis of 1,1-Dichloroalkenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1388-1393.
[4]	Liu Xu-Bo, Lin Jia-Le, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting. Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 663-668.
[5]	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.
[6]	Lu Yuhan, Han Yingzhi, Sun Yadong, Abdukader Ablimit, Wang Duozhi, Liu Chenjiang. Application of Iodobenzene Acetate Promoted Oxidation in the Synthesis of 2-Amino-1,3,4-thiadiazole Molecules [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 447-453.
[7]	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.
[8]	Cai Han, Ouyang Kunbing, Yang Nianfa. Application of Chiral 1,1'-Bi-2-naphthol Polymers in Asymmetric Epoxidation of (E)-α,β-Unsaturated Aryl Ketones [J]. Chin. J. Org. Chem., 2019, 39(5): 1456-1459.
[9]	Kong Shengnan, Qian Xuefeng, Shu Mouhai, Xiao Wende. Asymmetric Addition Reaction Catalyzed by 1- (2-Hydroxynaphtha-len-1-yl)naphthalen-2-ol Functionalized Porous Organic Polymer [J]. Chin. J. Org. Chem., 2018, 38(10): 2754-2760.
[10]	Yang Xiaojiang, Mao Jincheng, Zhang Heng, Zhang Yang, Mao Jinhua. Copper-Catalyzed Aerobic Oxidation Reaction of Benzyl Alcohol in Water under Base-Free Condition [J]. Chin. J. Org. Chem., 2018, 38(10): 2780-2783.
[11]	Wang Mincan. Enantioselective Analysis: Logic of Chiral Ligand Design for Asymmetric Addition of Diethylzinc to Benzaldehyde [J]. Chin. J. Org. Chem., 2018, 38(1): 162-170.
[12]	Zhang Wenfeng, Xu Zhaohui, Tu Yuanhong, Liao Chuanwen. Synthesis of 5,5-(Phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) Derivatives without Catalyst in Water [J]. Chin. J. Org. Chem., 2017, 37(9): 2449-2453.
[13]	Chen Diao, Xu Ming-Hua. Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Imines [J]. Chin. J. Org. Chem., 2017, 37(7): 1589-1612.
[14]	Lin Chunhua, Yuan Jianjun, Liu Deyong, Zhang Houfu, Xu Zhaohui. Efficient Synthesis of 5,5-(Phenylmethylene)bis(2,2-dimethyl-1,3-dioxane-4,6-dione) Derivatives in Biobased Gluconic Acid Aqueous Solution [J]. Chin. J. Org. Chem., 2017, 37(6): 1560-1564.
[15]	Zhang Xun, Yang Nianfa. Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes [J]. Chin. J. Org. Chem., 2017, 37(4): 1027-1032.