手性咪唑氨基醇的合成及其在铜催化不对称Henry反应中的应用

doi:10.6023/cjoc201807008

有机化学 ›› 2019, Vol. 39 ›› Issue (2): 443-448.DOI: 10.6023/cjoc201807008 上一篇下一篇

研究论文

手性咪唑氨基醇的合成及其在铜催化不对称Henry反应中的应用

毛璞^a, 杨亮茹^a, 肖咏梅^a, 袁金伟^a, 买文鹏^b, 高杰^a, 张心持^a

a 河南工业大学化学化工与环境学院河南省天然药物化学院士工作站郑州 450001;
b 河南工程学院材料工程学院郑州 451191

收稿日期:2018-07-04 修回日期:2018-08-31 发布日期:2018-09-26
通讯作者: 毛璞, 杨亮茹 E-mail:lryang@haut.edu.cn;maopu@haut.edu.cn
基金资助:
国家自然科学基金（No.21172055）、河南省教育厅自然科学基金（No.18A150004）、郑州市科技创新团队（No.131PCXTD605）和河南省高校基础研究和河南工业大学（No.2017RCJH08）资助项目.

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

Mao Pu^a, Yang Liangru^a, Xiao Yongmei^a, Yuan Jinwei^a, Mai Wenpeng^b, Gao Jie^a, Zhang Xinchi^a

a Academician Workstation for Natural Medicinal Chemistry of Henan Province, School of Chemical Engineering and Environment, Henan University of Technology, Zhengzhou 450001;
b School of Material and Chemical Engineering, Henan University of Engineering, Zhengzhou 451191

Received:2018-07-04 Revised:2018-08-31 Published:2018-09-26
Contact: 10.6023/cjoc201807008 E-mail:lryang@haut.edu.cn;maopu@haut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172055), the Natural Science Foundation of Henan Province Department of Education (No. 18A150004), the Program for Innovative Research Team from Zhengzhou City (No. 131PCXTD605), and the Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology (No. 2017RCJH08).

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1. 手性咪唑氨基醇的合成及其在铜催化不对称Henry反应中的应用.PDF(5030KB)

摘要/Abstract

以L-苯丙氨醇、连苯甲酰、醋酸铵及不同的杂芳醛为原料，经"四组分一锅煮"缩合反应合成了系列多芳基取代的手性咪唑氨基醇衍生物.X射线单晶衍射测定证明，在缩合反应中，L-苯丙氨醇的构型保持.将手性配体与Cu（OAc）₂·H₂O用于催化硝基甲烷与芳醛的不对称Henry反应，可以中等或高收率，高对映选择性（>99%）获得S构型的产物.此体系催化剂合成简单、反应条件温和、对映选择性高，有很好的应用前景.

关键词: 手性, 咪唑氨基醇, 不对称Henry反应

Using L-phenylalaninol as chiral precursor, a series of multi-aryl substituted imidazole amino alcohol derivatives containing appended chiral functionalities were synthesized through a "four component-one pot procedure" from the condensation reaction of L-phenylalaninol, dibenzoyl (benzil), ammonium acetate and different heterocyclic aryl-aldehyde. X-ray crystal analysis confirmed that the chiral carbon retained the S configuration of L-phenylalaninol. The chiral ligands in combination with Cu(OAc)₂·H₂O catalyzed the enantioselective Henry reaction of nitromethane and aromatic aldehydes with moderate to high yields and excellent enantioselectivities (>99%) with S configuration. The easy availability of catalyst components, mild reaction conditions and high enantioselectivity make the system attractive for practical application.

Key words: chiral, imidazole amino alcohol, asymmetric Henry reaction

引用此文

毛璞, 杨亮茹, 肖咏梅, 袁金伟, 买文鹏, 高杰, 张心持. 手性咪唑氨基醇的合成及其在铜催化不对称Henry反应中的应用[J]. 有机化学, 2019, 39(2): 443-448.

Mao Pu, Yang Liangru, Xiao Yongmei, Yuan Jinwei, Mai Wenpeng, Gao Jie, Zhang Xinchi. Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction[J]. Chin. J. Org. Chem., 2019, 39(2): 443-448.

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参考文献

[1] Rosini, G. In Comprehensive Organic Synthesis, Vol. 2, Eds.:Trost, B. M., Fleming, I., Pergamon, Oxford, UK, 1999, p. 321.
[2] Pinnick, H. W. In Organic Reactions, Vol. 38, Ed.:Paquette, L. A., Wiley, New York, 1990, Chapter 3.
[3] Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem. 2007, 2561.
[4] Ono, N. The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001.
[5] Shibasaki, M.; Gröger, H. In Comprehensive Asymmetric Catalysis, Vol. Ⅲ, Eds.:Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.; Springer, Berlin, Germany, 1999, p. 1075.
[6] Shibasaki, M.; Gröger, H.; Kanai, M. In Comprehensive Asymmetric Catalysis, Eds.:Supplement, I.; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Springer, Heidelberg, Germany, 2004, p. 131.
[7] Luzzio, F. A. Tetrahedron 2001, 57, 915.
[8] Bandini, M.; Piccinelli, F.; Tommasi, S.; Ronchi, A. U.; Ventrici, C. Chem. Commun. 2007, 616.
[9] Blay, G.; Hernández-Olmos, V.; Pedro, J. R. Synlett 2011, 1195.
[10] Palomo, C.; Oiarbide, M.; Mielgo, A. Angew. Chem., Int. Ed. 2004, 43, 5442.
[11] Zhang, S.; Li, Y.; Xu, Y.; Wang, Z. Chin. Chem. Lett. 2018, 29, 873.
[12] Bhatt, A. P.; Pathak, K.; Jasra, R. V.; Kureshy, R. I.; Khan, N. H.; Abdi, S. H. R. J. Mol. Catal. A:Chem. 2006, 244, 110.
[13] Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861.
[14] Palomo, C.; Oiarbide, M.; Laso, A. Angew. Chem., Int. Ed. 2005, 44, 3881.
[15] Liu, S. L.; Wolf, C. Org. Lett. 2008, 10, 1831.
[16] Bulut, A.; Aslan, A.; Dogan, Ö. J. Org. Chem. 2008, 73, 7373.
[17] Park, J.; Lang, K.; Abboud, K. A.; Hong, S. J. Am. Chem. Soc. 2008, 130, 16484.
[18] Kogami, Y.; Nakajima, T.; Ikeno, T.; Yamada, T. Synthesis 2004, 1947.
[19] Kowalczyk, R.; Kwiatkowski, P.; Skarzewski, J.; Jurczak, J. J. Org. Chem. 2009, 74, 753.
[20] Zulauf, A.; Mellah, M.; Schulz, E. J. Org. Chem. 2009, 74, 2242.
[21] Choudary, B. M.; Ranganath, K. V. S.; Pal, U.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 13167.
[22] Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418.
[23] Christensen, C.; Juhl, K.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4875.
[24] Xiong, Y.; Wang, F.; Huang, X.; Wen, Y.; Feng, X. Chem.-Eur. J. 2007, 13, 829.
[25] Bandini, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A.; Ventrici, C. Chem. Commun. 2007, 616.
[26] Arai, T.; Takashita, R.; Endo, Y.; Watanabe, M.; Yanagisawa, A. J. Org. Chem. 2008, 73, 4903.
[27] Ma, K.; You, J. Chem.-Eur. J. 2007, 13, 1863.
[28] Dixit, A.; Kumar, P.; Yadav, G. D.; Singh, S. Inorg. Chim. Acta 2018, 479, 240.
[29] Khlebnikova, T. B.; Konev, V. N.; Pai, Z. P. Tetrahedron 2018, 74, 260.
[30] Christensen, C.; Juhl, K.; Jørgensen, K. A. Chem. Commun. 2001, 2222.
[31] Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692.
[32] McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
[33] Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2006, 106, 3561.
[34] Hargaden, G. C.; Guiry, P. J. Chem. Rev. 2009, 109, 2505.
[35] Aydin, A. E.; Yuksekdanaci, S. Tetrahedron:Asymmetry 2013, 24, 14.
[36] Wolinska, E. Tetrahedron:Asymmetry 2014, 25, 1122.
[37] Cruz, H.; Aguirre, G.; Madrigal, D. Chavez, D.; Somanathan, R. Tetrahedron:Asymmetry 2016, 27, 1217.
[38] Liu, S.; Wolf, C. Org. Lett. 2008, 10, 1831.
[39] Spangler, K. Y.; Wolf, C. Org. Lett. 2009, 11, 4724.
[40] Toussaint, A.; Pfaltz, A. Eur. J. Org. Chem. 2008, 14, 459.
[41] Kowalczyk, R.; Sidorowicz, L.; Skarzewski, J. Tetrahedron:Asymmetry 2008, 19, 2310.
[42] Selvakumar, S.; Sivasankaran, D.; Singh, V. K. Org. Biomol. Chem. 2009, 7, 3156.
[43] Chunhong, Z.; Liu, F.; Gou, S. Tetrahedron:Asymmetry 2014, 25, 278.
[44] Cwiek, R.; Nideziejko, P.; Kaluza, Z. J. Org. Chem. 2014, 79, 1222.
[45] El-Asaad, B.; Metay, E.; Karame, I.; Lemaire, M. Mol. Catal. 2017, 435, 76.
[46] Jin, W.; Li, X.; Huang, Y.; Wu, F.; Wan, B. Chem.-Eur. J. 2010, 16, 8259.
[47] Otevrel, J.; Bobal, P. J. Org. Chem. 2017, 82, 8342.
[48] Wu, L.; Su, Y.; Chong, S.; Zhang, W.; Huang, D.; Wang, K.; Hu, Y. Chin. J. Org. Chem. 2017, 37, 936(in Chinese). (吴丽丽, 苏瀛鹏, 种思颖, 张为钢, 黄丹风, 王克虎, 胡雨来, 有机化学, 2017, 37, 936.)
[49] Blay, G.; Climent, E.; Fernández, I.; Hernández-Olmos, V.; Pedro, J. R. Tetrahedron:Asymmetry 2007, 18, 1603.
[50] Blay, G.; Hernández-Olmos, V.; Pedro, J. R. Chem. Commun. 2008, 4840.
[51] Arai, T.; Suzuki, K. Synlett 2009, 3167.
[52] Sappino, C.; Mari, A.; Mantineo, A.; Moliterno, M.; Palagri, M.; Tatangelo, C.; Suber, L.; Bovicelli, P.; Ricelli, A.; Righi, G. Org. Biomol. Chem. 2018, 16, 1860.
[53] Vicario, J.; Badia, D.; Carrillo, L.; Reyes E.; Etxebarria, J. Curr. Org. Chem. 2005, 9, 219.
[54] Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
[55] Guo, J.; Mao, J. Chirality 2009, 21, 619.
[56] Xu, F.; Lei, C.; Yan, L.; Tu, J.; Li, G. Chirality 2015, 27, 761.
[57] Lu, G.; Zheng, F.; Wang, L.; Guo, Y.; Li, X.; Cao, X.; Wang, C.; Chi, H.; Dong, Y.; Zhang, Z. Tetrahedron:Asymmetry 2016, 27, 732.
[58] Chen, W.; Zhou, Z., Chen, H. Org. Biomol. Chem. 2017, 15, 1530.
[59] Bao, W.; Wang, Z.; Li, Y. J. Org. Chem. 2003, 68, 591.
[60] Mao, P.; Cai, Y.; Xiao, Y.; Yang, L.; Xue, Y.; Song, M. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 2418.
[61] Matsuoka, Y.; Ishida, Y.; Sasaki, D.; Saigo, K. Tetrahedron 2006, 62, 8199.
[62] Xiao, Y.; Yang, L.; He, K.; Yuan, J.; Mao, P. Acta Crystallogr. 2012, E68, o264.
[63] Yang, L.; Xiao, Y.; He, K.; Yuan, J.; Mao, P. Acta Crystallogr. 2012, E68, o1670.
[64] Kodama, K.; Sugawara, K.; Hirose, T. Chem.-Eur. J. 2011, 17, 13584.

手性咪唑氨基醇的合成及其在铜催化不对称Henry反应中的应用

Synthesis of Chiral Imidazole Amino Alcohols and Their Application in the Asymmetric Copper-Catalyzed Henry Reaction

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