不对称合成手性3,5-二取代脯氨酸及其衍生物

doi:10.6023/cjoc201712005

有机化学 ›› 2018, Vol. 38 ›› Issue (6): 1437-1446.DOI: 10.6023/cjoc201712005 上一篇下一篇

研究论文

不对称合成手性3,5-二取代脯氨酸及其衍生物

赵亮^a,b,c, 周圣斌^a,b, 童军华^a,b,c, 王江^a,b, 柳红^a,b

a 中国科学院上海药物研究所新药研究国家重点实验室和受体结构与功能重点实验室上海 201203;
b 中国科学院大学北京 100049;
c 中国科学技术大学苏州纳米学院苏州 215123

收稿日期:2017-12-04 修回日期:2018-02-12 发布日期:2018-02-28
通讯作者: 王江,E-mail:hliu@simm.ac.cn;柳红,E-mail:jwang@simm.ac.cn E-mail:hliu@simm.ac.cn;jwang@simm.ac.cn
基金资助:
国家自然科学基金（Nos.81620108027，21632008，21672231，21472209）、国家重大科学计划（No.2015CB910304）和上海市科委课题（No.15QA1404400）资助项目.

Asymmetric Synthesis of 3, 5-Disubstituted Prolines

Zhao Liang^a,b,c, Zhou Shengbin^a,b, Tong Junhua^a,b,c, Wang Jiang^a,b, Liu Hong^a,b

a State Key Laboratory of Drug Research and CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203;
b University of Chinese Academy of Sciences, Beijing 100049;
c Nano Science and Technology Institute, University of Science and Technology of China, Suzhou 215123

Received:2017-12-04 Revised:2018-02-12 Published:2018-02-28
Contact: 10.6023/cjoc201712005 E-mail:hliu@simm.ac.cn;jwang@simm.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 81620108027, 21632008, 21672231, 21472209), the Major Project of Chinese National Programs for Fundamental Research and Development (No. 2015CB910304) and the Shanghai Science and Technology Development Fund (No. 15QA1404400).

文章分享

1. 不对称合成手性3,5-二取代脯氨酸及其衍生物.PDF(3536KB)

摘要/Abstract

选用甘氨酸等当体镍螯合物与α，β-不饱和酮进行不对称Michael加成反应，在室温条件下，以1，8-二氮杂二环十一碳-7-烯（DBU）为碱，甲醇为溶剂，不对称合成了3，5-二取代脯氨酸及其衍生物.该方法具有操作简单、收率高、底物适用范围广的特点，为3，5-二取代脯氨酸及其衍生物的不对称合成提供了新的研究思路.

关键词: 3,5-二取代脯氨酸, 甘氨酸等当体镍螯合物, 不对称Michael加成反应

Highly diastereoselective Michael addition reactions of chiral Ni(Ⅱ)-complex of glycine with α,β-unsaturated ketones in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and MeOH at ambient temperature were achieved. The operationally convenient procedure for preparation of the target products renders that this method is an attractive strategy for practical synthesis of 3,5-disubstituted prolines.

Key words: 3,5-disubstituted proline, Ni (II)-complex of glycine, asymmetric Michael addition

引用此文

赵亮, 周圣斌, 童军华, 王江, 柳红. 不对称合成手性3,5-二取代脯氨酸及其衍生物[J]. 有机化学, 2018, 38(6): 1437-1446.

Zhao Liang, Zhou Shengbin, Tong Junhua, Wang Jiang, Liu Hong. Asymmetric Synthesis of 3, 5-Disubstituted Prolines[J]. Chin. J. Org. Chem., 2018, 38(6): 1437-1446.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Fan, H.; Peng, J.; Hamann, M. T.; Hu, J. F. Chem. Rev. 2008, 108, 264.
(b) Najera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584.
[2] Viso, A.; Fernandez de la Pradilla, R.; Garcia, A.; Flores, A. Chem. Rev. 2005, 105, 3167.
[3] O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
[4] (a) Komatsubara, M.; Umeki, T.; Fukuda, T.; Iwao, M. J. Org. Chem. 2014, 79, 529.
(b) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Dwornik, K. A.; Petrich, S. A.; Du, K. X.; Bruce, M. A.; Vu, P.; Vargas, M.; Keertikar, K. M.; Hosein, K. N.; Jones, C. R.; Sikorski, J. A. Tetrahedron 1998, 54, 5075.
[5] Cheng, G. L.; Wang, X. Y.; Bao, H. L.; Cheng, C. J.; Liu, N.; Hu, Y. F. Org. Lett. 2012, 14, 1949.
[6] (a) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
(b) Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
(c) Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573.
[7] (a) Yu, Y. Y.; Wang, C. Y.; He, X. Z.; Yao, X. T.; Zu, L. S. Org. Lett. 2014, 16, 3580.
(b) Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587.
(c) Hua, M. Q.; Wang, L. A.; Cui, H. F.; Nie, J.; Zhang, X. L.; Ma, J. A. Chem. Commun. 2011, 47, 1632.
[8] (a) Wen, S.; Li, X.; Yao, W. J.; Waheed, A.; Ullah, N.; Lu, Y. X. Eur. J. Org. Chem. 2016, 25, 4298.
(b) Imbri, D.; Netz, N.; Kucukdisli, M.; Kammer, L. M.; Jung, P.; Kretzschmann, A.; Opatz, T. J. Org. Chem. 2014, 79, 11750.
(c) Bai, X. F.; Li, L.; Xu, Z.; Zheng, Z. J.; Xia, C. G.; Cui, Y. M.; Xu, L. W. Chem.-Eur. J. 2016, 22, 10399.
(d) Riano, I.; Diaz, E.; Uria, U.; Reyes, E.; Carrillo, L.; Vicario, J. L. Chem. Commun. 2016, 52, 2330.
[9] (a) Deng, G.; Wang, J.; Zhou, Y.; Jiang, H.; Liu, H. J. Org. Chem. 2007, 72, 8932.
(b) Ding, X.; Wang, H.; Wang, J.; Wang, S.; Lin, D.; Lv, L.; Zhou, Y.; Luo, X.; Jiang, H.; Acena, J. L.; Soloshonok, V. A.; Liu, H. Amino Acids 2013, 44, 791.
(c) Ding, X.; Ye, D.; Liu, F.; Deng, G.; Liu, G.; Luo, X.; Jiang, H.; Liu, H. J. Org. Chem. 2009, 74, 5656.
(d) Li, T. T.; Zhou, S. B.; Wang, J.; Acena, J. L.; Soloshonok, V. A.; Liu, H. J. Org. Chem. 2015, 80, 11275.
(e) Li, T. T.; Zhou, S. B.; Wang, J.; Acena, J. L.; Soloshonok, V. A.; Liu, H. Chem. Commun. 2015, 51, 1624.
(f) Lin, D.; Deng, G.; Wang, J.; Ding, X.; Jiang, H.; Liu, H. J. Org. Chem. 2010, 75, 1717.
(g) Lin, D.; Lv, L.; Wang, J.; Ding, X.; Jiang, H.; Liu, H. J. Org. Chem. 2011, 76, 6649.
(h) Nian, Y.; Wang, J.; Zhou, S.; Wang, S.; Moriwaki, H.; Kawashima, A.; Soloshonok, V. A.; Liu, H. Angew. Chem., Int. Ed. 2015, 54, 12918.
(i) Wang, J.; Lin, D. Z.; Shi, J. M.; Ding, X.; Zhang, L.; Jiang, H. L.; Liu, H. Synthesis 2010, 1205.
(j) Wang, J.; Liu, H.; Acena, J. L.; Houck, D.; Takeda, R.; Moriwaki, H.; Sato, T.; Soloshonok, V. A. Org. Biomol. Chem. 2013, 11, 4508.
(k) Wang, J.; Shi, T.; Deng, G.; Jiang, H.; Liu, H. J. Org. Chem. 2008, 73, 8563.
(l) Wang, J.; Zhang, L.; Jiang, H.; Chen, K.; Liu, H. Chimia 2011, 65, 919.
(m) Zhou, S.; Wang, J.; Chen, X.; Acena, J. L.; Soloshonok, V. A.; Liu, H. Angew. Chem., Int. Ed. 2014, 53, 7883.
(n) Deng, G. H.; Ye, D. J.; Li, Y. Y.; He, L. Y.; Zhou, Y.; Wang, J.; Li, J.; Jiang, H. L.; Liu, H. Tetrahedron 2008, 64, 10512.
(o) Lin, D.; Lv, L.; Wang, J.; Ding, X.; Jiang, H. L.; Liu, H. Chin. J. Chem. 2011, 76, 6649.
(p) Chen, H.; Wang, J.; Zhou, S.; Liu, H. Chin. J. Chem. 2014, 79, 7872.
[10] (a) Belokon, Y. N.; Bulychev, A. G.; Vitt, S. V.; Struchkov, Y. T.; Batsanov, A. S.; Timofeeva, T. V.; Tsyryapkin, V. A.; Ryzhov, M. G.; Lysova, L. A.; Bakhmutov, V. I.; Belikov, V. M. J. Am. Chem. Soc. 1985, 107, 4252.
(b) Belokon, Y. N.; Sagyan, A. S.; Djamgaryan, S. A.; Bakhmutov, V. I.; Vitt, S. V.; Batsanov, A. S.; Struchkov, Y. T.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 11990, 2301.
(c) Belokon, Y. N.; Sagyan, A. S.; Djamgaryan, S. M.; Bakhmutov, V. I.; Belikov, V. M. Tetrahedron 1988, 44, 5507.
(d) Soloshonok, V. A.; Kukhar, V. P. Tetrahedron 1996, 52, 6953.
(e) Soloshonok, V. A.; Kukhar, V. P.; Galushko, S. V.; Svistunova, N. Y.; Avilov, D. V.; Kuzmina, N. A.; Raevski, N. I.; Struchkov, Y. T.; Pysarevsky, A. P.; Belokon, Y. N. J. Chem. Soc., Perkin Trans. 11993, 3143.
[11] (a) Belokon, Y. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. A.; Belikov, V. M. J. Chem. Soc., Perkin Trans 1 1988, 8, 2075.
(b) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed. 2000, 39, 2172.
(c) Soloshonok, V. A.; Cai, C. Z.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 9645.
(d) Cai, C. Z.; Soloshonok, V. A.; Hruby, V. J. J. Org. Chem. 2001, 66, 1339.
(e) Magdesieva, T. V.; Levitskiy, O. A.; Grishin, Y. K.; Ambartsumyan, A. A.; Kiskin, M. A.; Churakov, A. V.; Babievsky, K. K.; Kochetkov, K. A. Organometallics 2014, 33, 4629.
[12] (a) Belokon, Y. N.; Popkov, A. N.; Chernoglazova, N. I.; Saporovskaya, M. B.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Chem. Commun. 1988, 19, 1336.
(b) Soloshonok, V. A.; Tang, X. J.; Hruby, V. J.; Van Meervelt, L. Org. Lett. 2001, 3, 341.
(c) Taylor, S. M.; Yamada, T.; Ueki, H.; Soloshonok, V. A. Tetrahedron Lett. 2004, 45, 9159.
(d) Gu, X. Y.; Tang, X. J.; Cowell, S.; Ying, J. F.; Hruby, V. J. Tetrahedron Lett. 2002, 43, 6669.
[13] (a) Wang, Y. B.; Song, X. H.; Wang, J. Moriwaki, H.; Soloshonok, V. A.; Liu, H. Amino Acids 2017, 49, 1487.
(b) Wang, J.; Deng, G. H.; Liu, H.; Jiang, H. L. Chin. J. Org. Chem. 2008, 28, 1138(in Chinese). (王江, 邓光辉, 柳红, 蒋华良, 有机化学, 2008, 28, 1138.)

不对称合成手性3,5-二取代脯氨酸及其衍生物

Asymmetric Synthesis of 3, 5-Disubstituted Prolines

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 1

编辑推荐

相关统计

本文评价