Recent Advances in Asymmetric Synthesis of Optically Active Indole Derivatives from 3-Indolylmethanols

doi:10.6023/cjoc201510024

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (6): 1229-1240.DOI: 10.6023/cjoc201510024 Previous Articles Next Articles

Reviews

基于吲哚-3-基甲醇不对称合成光学活性吲哚衍生物研究进展 2017-2018 Awarded

朱帅^b, 徐鲁斌^b, 王亮^a,b, 肖建^a,b

a 荆楚理工学院药物合成与优化湖北省重点实验室荆门 448000;
b 青岛农业大学化学与药学院青岛 266109

收稿日期:2015-10-21 修回日期:2015-12-15 发布日期:2016-02-01
通讯作者: 王亮, 肖建 E-mail:chemjianxiao@163.com
基金资助:
荆楚理工学院药物合成与优化湖北省重点实验室开放基金(Nos.OPP2015YB01,OPP2015ZD02)、青岛农业大学高层次人才启动基金(Nos.6631112323,6631115015)资助项目.

Recent Advances in Asymmetric Synthesis of Optically Active Indole Derivatives from 3-Indolylmethanols

Zhu Shuai^b, Xu Lubin^b, Wang Liang^a,b, Xiao Jian^a,b

aHubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology, Jingmen 448000;
b College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109

Received:2015-10-21 Revised:2015-12-15 Published:2016-02-01
Supported by:
Project supported by the Open Project Program of Hubei Key Laboratory of Drug Synthesis and Optimization Jingchu University of Technology (Nos. OPP2015YB01, OPP2015ZD02), the Talents of High Level Scientific Research Foundation of Qingdao Agricultural University (Nos. 6631112323, 6631115015).

The electrophilic intermediate, vinylogous imine or vinylogous iminium, can be in situ generated from 3-indolyl- methanols under acidic conditions. With the aid of chiral catalysts, miscellaneous nucleophiles can attack these electrophilic intermediates to afford enantioenriched and biologically important 3-substituted indole derivatives. The recent advances of preparation of optically active indole derivatives from 3-indolylmethanols via asymmetric alkylation, asymmetric reduction and asymmetric rearrangement are summarized.

Key words: 3-indolylmethanol, optically active, indole derivatives, asymmetric synthesis

Cite this article

Zhu Shuai, Xu Lubin, Wang Liang, Xiao Jian. Recent Advances in Asymmetric Synthesis of Optically Active Indole Derivatives from 3-Indolylmethanols[J]. Chin. J. Org. Chem., 2016, 36(6): 1229-1240.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Lo, K. K.-W.; Tsang, K. H.-K.; Hui, W.-K.; Zhu, N. Chem. Commun. 2003, 2704.
[2] Plimmer, J. R.; Gammon, D. W.; Ragsdale, N. N. Encyclopedia of Agrochemicals, Vol. 3, John Wiley & Sons, New York, 2003.
[3] Ramirez, A.; Garcia-Rubio, S. Curr. Med. Chem. 2003, 10, 1891.
[4] Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489.
[5] Goveky, S. P.; Overman, L. E. Tetrahedron 2007, 63, 8499.
[6] (a) Lancianesi, S.; Palmoeri, A.; Petrini, M. Chem. Rev. 2014, 114, 7108.
(b) Shiri, M.; Zolfigol, M. A. Chem. Rev. 2010, 110, 2250.
(c) Bartoli, G.; Bencivenni, G.; Dalpozzo, R. Chem. Soc. Rev. 2010, 39, 4449.
[7] Ramesh, C.; Kavala, V.; Kuo, C. W.; Rama, R. B.; Yao, C. F. Eur. J. Org. Chem. 2010, 2010, 3796.
[8] Furstner, A.; Radkowski, K.; Peters, H. Angew. Chem., Int. Ed. 2005, 44, 2777.
[9] Usami, Y.; Yamaguchi, J.; Numata, A. Heterocycles 2004, 63, 1123.
[10] Zhan, Z. P.; Yang, R. F.; Lang, K. Tetrahedron Lett. 2005, 46, 3859.
[11] Auria, M. Tetrahedron 1991, 47, 9225.
[12] Rabindran, S. K.; Ross, D. D.; Doyle, L. A.; Yang, W. D.; Greenberger, L. M. Cancer Res.2000 ,60, 47.
[13] Bergman, J.; Venemalm, L. Tetrahedron Lett. 1988, 29, 2993.
[14] Richou, R. M.; Lallouette, P.; Richou, H. C.R. Acad. Sci. 1967, 264, 2426.
[15] Usami, Y.; Yamaguchi, J.; Numata, A. Heterocycles 2004, 63, 1123.
[16] Conn, P., M.; Crowley, W. F., Jr. Annu. Rev. Med. 1994, 45, 391.
[17] (a) Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed.2009, 48, 9608.
(b) Bartoli, G.; Bencivenni, G.; Dalpozzo, R. Chem. Soc. Rev. 2010, 39, 4449.
(c) Zeng, M.; You, S.-L. Synlett 2010, 1289
[18] (a) Lyttle, D. A.; Weisblat, D. I. J. Am. Chem. Soc. 1947, 69, 2118.
(b) Semenov, B. B.; Granik, V. G. Pharm. Chem. J. 2004, 38, 287.
(c) Palmieri, A.; Petrini, M.; Shaikh, R. R. Org. Biomol. Chem. 2010, 8, 1259.
(d) Wang, L.; Chen, Y.-Y.; Xiao, J. Asian J. Org. Chem. 2014, 3, 1036.
[19] Kataja, A. O.; Masson, G. Tetrahedron 2014, 70, 8783.
[20] Cozzi, P. G.; Benfatti, F.; Zoli, L. Angew. Chem., Int. Ed. 2009, 48, 1313.
[21] Zhang, Y.; Wang, S.-Y.; Xu, X.-P.; Jiang, R.; Ji, S.-J. Org. Biomol. Chem. 2013, 11, 1933.
[22] Xiao, J.; Zhao, K.; Loh, T.-P. Chem. Asian J. 2011, 6, 2890.
[23] (a) Bandini, M.; Tragni, M. Org. Biomol. Chem. 2009, 7, 1501.
(b) Emer, E.; Sinisi, R.; Capdevila, M. G.; Petruzziello, D.; De Vincentiis, F.; Cozzi, P. G. Eur. J. Org. Chem. 2011, 2011, 647.
(c) Cozzi, P.; Gualandi, A. Synlett 2013, 24, 281.
(d) Kumar, R.; Eycken, E. V. V. d. Chem. Soc. Rev. 2013, 42, 1121.
[24] (a) Xiao, J. Org. Lett. 2012, 14, 1716.
(b) Xiao, J.; Zhao, K.; Loh, T.-P. Chem. Commun. 2012, 48, 3548.
[25] Han, B.; Xiao, Y.-C.; Yao, Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2010, 49, 10189.
[26] Xiao, Y.-C.; Zhou, Q.-Q.; Dong, L.; Liu, T.-Y.; Chen, Y.-C. Org. Lett. 2012, 14, 5940.
[27] Xu, B.; Guo, Z. L.; Jin, W. Y.; Wang, Z. P.; Peng, Y. G.; Guo, Q. X. Angew. Chem., Int. Ed. 2012, 51, 1059.
[28] Zhang, C.; Zhang, L.-X.; Qiu, Y.; Xu, B.; Zong, Y.; Guo, Q.-X. RSC Adv. 2014, 4, 6916.
[29] Tan, W.; Li, X.; Gong, Y.-X.; Ge, M.-D.; Shi, F. Chem. Commun. 2014, 50, 15901
[30] Shi, F.; Zhang, H.-H.; Sun, X.-X.; Liang, J.; Fan, T.; Tu, S.-J. Chem. Eur. J. 2015, 21, 3465
[31] Guo, Q.-X.; Peng, Y.-G.; Zhang, J.-W.; Song, L.; Feng, Z.; Gong, L.-Z. Org. Lett. 2009, 11, 4620.
[32] Guo, C.; Song, J.; Huang, J.-Z.; Chen, P.-H.; Luo, S.-W.; Gong, L.-Z. Angew. Chem., Int. Ed. 2012, 51, 1046.
[33] Tan, W.; Du, B.-X.; Li, X.; Zhu, X.; Shi, F.; Tu, S.-J. J. Org. Chem. 2014, 79, 4635
[34] Song, J.; Guo, C.; Adele, A.; Yin, H.; Gong, L. Z. Chem. Eur. J. 2013, 19, 3319.
[35] Song, L.; Guo, Q.-X.; Li, X.-C.; Tian, J.; Peng, Y.-G. Angew. Chem., Int. Ed. 2012, 124, 1935.
[36] Ren, C.-L.; Zhang, T.; Wang, X.-Y.; Wu, T.; Ma, J.; Xuan, Q.-Q.; Wei, F.; Huang, H.-Y.; Wang, D.; Liu, L. Org. Biomol. Chem. 2014, 12, 9881.
[37] Guo, Z.-L.; Xue, J.-H.; Fu, L.-N.; Zhang, S.-E.; Guo, Q.-X. Org. Lett. 2014, 16, 6472.
[38] Xu, B.; Shi, L.-L.; Zhang, Y.-Z.; Wu, Z.-J.; Fu, L.-N.; Luo, C.-Q.; Zhang, L.-X.; Peng, Y.-G.; Guo, Q.-X. Chem. Sci. 2014, 5, 1988.
[39] Ma, J.-A.; Dong, X.-D.; Li, S.; Guo, R.; Nie, J. Org. Lett. 2015, 17, 1389.
[40] Shi, F.; Tu, S. J.; Zhu, R.Y. Chem. Eur. J. 2014, 20, 2597.
[41] Dai, W.; Lu, H.; Li, X.; Shi, F.; Tu, S.-J. Chem. Eur. J. 2014, 20, 11382.
[42] Rueping, M.; Nachtsheim, B. J.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593.
[43] Zhuo, M.-H.; Jiang, Y.-J.; Fan, Y.-S.; Gao, Y.; Liu, S.; Zhang, S. Org. Lett. 2014, 16, 1096.
[44] Sun, X.-X.; Du, B.-X.; Zhang, H.-H.; Ji, L.; Shi, F. ChemCatChem 2015, 7, 1211.
[45] Sun, F.-L., Gu. Q.; Zeng, M.; You, S.-L. Chem. Eur. J. 2009, 15, 8709.
[46] Wang, S.-G.; Han, L.; Zeng, M.; Sun, F.-L.; Zhang, W.; You, S.-L. Org. Biomol. Chem. 2012, 10, 3202.
[47] Wang, D.-S.; Tang, J.; Zhou, Y.-G.; Chen, M.-W.; Yu, C.-B.; Duan, Y.; Jiang, G.-F. Chem. Sci. 2011, 2, 803.
[48] Duan, Y.; Chen, M.-W.; Ye, Z.-S.; Wang, D.-S.; Chen, Q.-A.; Zhou, Y.-G. Chem. Eur. J. 2011, 17, 7193.
[49] Liang, T.; Zhang, Z.; Antilla, J. C. Angew. Chem., Int. Ed. 2010, 49, 9734.
[50] Non-asymmetric alkylation and arylation of 3-indolylmethanol were implemented in our group under catalyst-free condition with water and trifluoroethanol as reaction media:
(a) Wen, H.; Wang, L.; Xu, L.; Hao, Z.; Shao, C.-L.; Wang, C.-Y.; Xiao, J. Adv. Synth. Catal. 2015, 357, 4023.
(b) Xiao, J.; Wen, H.; Wang, L.; Xu, L.; Hao, Z.; Shao, C.-L.; Wang, C.-Y. Green Chem. 2016, 18, 1032.

基于吲哚-3-基甲醇不对称合成光学活性吲哚衍生物研究进展 2017-2018 Awarded

Recent Advances in Asymmetric Synthesis of Optically Active Indole Derivatives from 3-Indolylmethanols

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[2]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[3]	Yuchao Wang, Jinbiao Liu, Zhitao He. Palladium-Catalyzed Asymmetric Hydrofunctionalizations of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2614-2627.
[4]	Tingyu Song, Ran Li, Lihua Huang, Shikun Jia, Guangjian Mei. Catalytic Asymmetric Synthesis of N—N Atropisomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1977-1990.
[5]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[6]	Ling Meng, Jun Wang. Research Progress on Synthesis of Thioflavonoids [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 873-891.
[7]	Qian Wang, Yuqi Liu, Zongquan Wu. Synthesis and Structure Control of Chiral Helical Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4141-4146.
[8]	Meijiao Sun, Jing Tan, Yu Tan, Jinsong Peng, Chunxia Chen. Pd-Catalyzed C(2)—H Arylation of 3-(2-Aminopyrimidin-4-yl)indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3945-3959.
[9]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[10]	Liu-Yang Pu, Zhiyue Li, Limin Li, Yucui Ma, Min Ma, Shengquan Hu, Zhengzhi Wu. Asymmetric Synthesis of (–)-Colchicine and Its Natural Analog (–)-N-Acetylcolchicine Methyl Ether [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 313-319.
[11]	Yuanhao Mao, Yanfeng Gao, Zhiwei Miao. Research Progress on the Asymmetric Cyclization Synthesis of Seven-Membered Rings via Transition Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1904-1924.
[12]	Zexin Huang, Yuqiang Yin, Fengcheng Jia, Anxin Wu. Research Progress on C2—C3 Bond Cleavage of Indole and Its Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2028-2044.
[13]	Ting Yao, Jiayan Li, Jiaming Wang, Changgui Zhao. Recent Advances for the Construction of Seven-Membered Ring Catalyzed by N-Heterocyclic Carbenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 925-944.
[14]	Lihua Wang, Xushun Gong, Ting Lei, Shizhi Jiang. Research Progress on Asymmetric Synthesis of Flavanones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 758-769.
[15]	Xiuliang Cheng, Dong Li, Boxuan Yang, Yumei Lin, Lei Gong. Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3335-3350.