Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes

doi:10.6023/cjoc201611027

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 1027-1032.DOI: 10.6023/cjoc201611027 Previous Articles Next Articles

Notes

聚[(S)-3-丙烯酰胺基-2,2'-二羟基-1,1'-联萘]的合成及催化二乙基锌与芳基醛不对称加成反应中的应用

张勋, 阳年发

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:2016-11-22 修回日期:2016-12-15 发布日期:2017-01-04
通讯作者: 阳年发 E-mail:nianfayang@xtu.edu.cn

Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes

Zhang Xun, Yang Nianfa

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

Received:2016-11-22 Revised:2016-12-15 Published:2017-01-04
Contact: 10.6023/cjoc201611027 E-mail:nianfayang@xtu.edu.cn

1. Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes.PDF(1376KB)

Abstract

Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl] (poly-6) was synthesized through radical polymerization and applied in the asymmetric addition of diethylzinc to aromatic aldehydes, giving the optically active products up to 95% enantiomeric excess (ee). Besides, The poly-6 could be recycled up to six times without erosion of the enantioselectivity.

Key words: polyacrylamide, 1,1'-bi-2-naphthol, Et₂Zn, aromatic aldehydes, asymmetric addition

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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.

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[1] Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
[2] 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.)
[3] (a) Yu, H. B.; Hu, Q. S.; Pu. L. J. Am. Chem. Soc. 2000, 122, 6500.
(b) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J. I. Tetrahedron Lett. 1998, 39, 3783.
(c) Rheiner, P. B.; Seebach, D. Chem. Eur. J. 1999, 5, 3221.
(d) Hu, Q. S.; Pugh, V.; Sabat, M.; Pu, L. J. Org. Chem. 1999, 64, 7528.
(e) Kollner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274.
[4] Liu, D. C.; Zhu, W. J.; Zhang, A. L.; Yang, N. F.; Yang, L. W. Chin. J. Org. Chem. 2015, 35, 1797 (in Chinese).
(刘大财, 朱维君, 张安林, 阳年发, 杨利文, 有机化学, 2015, 35, 1797.)
[5] Arai, T.; Hu, Q. S.; Zheng, X. F.; Pu, L.; Sasai, H. Org. Lett. 2000, 2, 4261.
[6] Zhang, A. L.; Yu, Z. D.; Yang, N. F.; Yang, L. W. Tetrahedron: Asymmetry 2015, 26, 173.
[7] (a) Harada, T.; Kanda, K. Org. Lett. 2006, 8, 3817.
(b) Chen, Y. H.; Qin, G. C.; Yang, L. W.; Yang, N. F. Chin. J. Chem. 2015, 33, 463.
(c) Chen, Y. H.; Cheng, D. J.; Zhang, J.; Wang, Y.; Liu, X. Y.; Tan, B. J. Am. Chem. Soc, 2015, 137, 15062.
[8] Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889.
[9] Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
[10] Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 9626.
[11] Ishii, A.; Soloshonok, V. A.; Mikami, K. J. Org. Chem. 2000, 65, 1597.
[12] Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
[13] Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
[14] Gou, S. H.; Judeh, Z. M. A. Tetrahedron Lett. 2009, 50, 281.
[15] 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.
[16] Sokeirik, Y. S.; Omote, M.; Sato, K.; Kamadaki, I.; Ando, A. Tetrahedron: Asymmetry 2006, 17, 2654.
[17] Priego, J.; Mancheno, O. G.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346.
[18] Tanaka, T.; Yasuda, Y.; Hayashi, M. J. Org. Chem. 2006, 71, 7091.
[19] Cabrera, S.; Carretero, J. C. Chem. Commun. 2001, 2026.
[20] Manabu, H.; Takashi, M.; Kazuaki, I. J. Org. Chem. 2006, 71, 6474. Zhang, A. L.; Liu, Y. L.; Yang, N. F.; Yang, L. W. Tetrahedron: Asymmetry 2014, 24, 289.

聚[(S)-3-丙烯酰胺基-2,2'-二羟基-1,1'-联萘]的合成及催化二乙基锌与芳基醛不对称加成反应中的应用

Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes

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