中文
Announcement
More
Progress in Chemistry 2016, Vol. 28 Issue (6): 801-813 DOI: 10.7536/PC160102 Previous Articles   Next Articles

• Review and comments •

Catalytic Asymmetric Syntheses of Indenes and Their Derivatives

He Qiao2, Yin Zhongqiong3, Chen Huabao2, Zhang Zumin1, Wang Xianxiang1, Yue Guizhou1,2*   

  1. 1. College of Science, Sichuan Agricultural University, Ya'an 625014, China;
    2. College of Agricultural Sciences, Sichuan Agricultural University, Chengdu 611130, China;
    3. College of Veterinary Medicine, Sichuan Agricultural University, Chengdu 611130, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the Science & Technology Department of Sichuan Province (No. 2012JY0118) and the "dual support" Project of Sichuan Agricultural University.
PDF ( 1085 ) Cited
Export

EndNote

Ris

BibTeX

Indenes and their derivatives widely exists in natural world, and some of them bearing multi-functional groups are very potential to become the lead compounds in drug because of their important bioactivities. In particular, asymmetric syntheses of indenes have attracted the extensive attention of organic chemists. Recently, many synthetic methods of them have been reported, including resolution of racemic mixture, syntheses of chiral auxiliary or substrate's induction, as well as chiral catalytic synthesis. In this review, we summarize the asymmetric syntheses of these compounds, and focus on the transition metal-catalyzed and organocatalytic asymmetric reaction. Finally, the further research on this field is also discussed.

Contents
1 Introduction
2 Catalytic asymmetric syntheses of indenes and their derivatives
2.1 Indene
2.2 Indanone
2.3 Indane
2.4 Indanol
2.5 Other derivatives
3 Conclusion

CLC Number: 

[1] Minegishi H, Futamura Y, Fukashiro S, Muroi M, Kawatani M, Osada H, Nakamura H. J. Med. Chem., 2015, 58: 4230.
[2] Conlon K, Christy C, Westbrook S, Whitlock G, Roberts L, Stobie A, McMurray G. J. Pharmacol. Exp. Ther., 2009, 330: 892.
[3] Apparsundaram S, Stockdale D J, Henningsen R A, Milla M E, Martin R S. J. Pharmacol. Exp. Ther., 2008, 327: 982.
[4] Svendsen O, Arnt J, Boeck V, Bøgesø K, Christensen A, Hyttel J, Larsen J J. Drug Dev. Res., 1986, 7: 35.
[5] Treinen K, Louden C, Dennis M, Wier P. Teratology, 1999, 59: 51.
[6] Ohlstein E H, Nambi P, Lago A, Hay D, Beck G, Fong K L, Eddy E P, Smith P, Ellens H, Elliott J D. J. Pharmacol. Exp. Ther., 1996, 276: 609.
[7] Barone F, White R, Elliott J, Feuerstein G, Ohlstein E. J. Cardiovasc. Pharmacol., 1995, 26: 404.
[8] Vlasses P H, Irvin J D, Huber P B, Lee R B, Ferguson R K, Schrogie J J, Zacchei A G, Davies R O, Abrams W B. Clin. Pharmacol. Ther., 1981, 29: 798.
[9] Davies I W, Senanayake C H, Larsen R D, Verhoeven T R, Reider P J. Tetrahedron Lett., 1996, 37: 1725.
[10] Kurosu M, Porter J R, Foley M A. Tetrahedron Lett., 2004, 45: 145.
[11] Kerr M S, de Alaniz J R, Rovis T. J. Org. Chem., 2005, 70: 5725.
[12] He M, Struble J R, Bode J W. J. Am. Chem. Soc., 2006, 128: 8418.
[13] Struble J R, Kaeobamrung J, Bode J W. Org. Lett., 2008, 10: 957.
[14] Boger D L, Hueter O, Mbiya K, Zhang M. J. Am. Chem. Soc., 1995, 117: 11839.
[15] Hong B, Li C, Wang Z, Chen J, Li H, Lei X. J. Am. Chem. Soc., 2015, 137: 11946.
[16] Shi Y, Yang B, Cai S, Gao S. Angew. Chem. Int. Ed., 2014, 53: 9539.
[17] Thommen C, Jana C K, Neuburger M, Gademann K. Org. Lett., 2013, 15: 1390.
[18] Deng J, Zhou S, Zhang W, Li J, Li R, Li A. J. Am. Chem. Soc., 2014, 136: 8185.
[19] Kheira H, Li P, Xu J. J. Mol. Catal. A: Chem., 2014, 391: 168.
[20] Hu J, Yan J, Chen J, Pang Y, Li X. MedChemComm, 2015, 6: 1318.
[21] Da Silva Barbosa J, Da Silva G V J, Constantino M G. Tetrahedron Lett., 2015, 56: 4649.
[22] Sudhakar G, Satish K. Chem.Eur. J., 2015, 21: 6475.
[23] Cai S, Xiao Z, Shi Y, Gao S. Chem.Eur. J., 2014, 20: 8677.
[24] Taylor J G, da Silva Ribeiro R, Correia C R D. Tetrahedron Lett., 2011, 52: 3861.
[25] Gabriele B, Mancuso R, Veltri L. Chem.Eur. J., 2016, 22:5056.
[26] 丁奎岭(Ding K L), 范青华(Fan Q H). 化学通讯(Chemical Newsletter), 2009,(6): 22.
[27] 麻远(Ma Y), 殷巍(Yin W), 赵玉芬(Zhao Y F). 有机化学(Chinese Journal of Organic Chemistry), 2008, 28(1): 37.
[28] 柴凤兰(Chai F L), 徐海云(Xu H Y). 化工进展(Chemical Industry and Enginerring Progress), 2014, 33(11): 3045.
[29] 段义杰(Duan Y J), 刘建利(Liu J L), 王翠玲(Wang C L). 有机化学(Chinese Journal of Organic Chemistry), 2010, 30(7): 988.
[30] Vilums M, Heuberger J, Heitman L H, IJzerman A P. Med. Res. Rev., 2015, 35: 1097.
[31] Enders M, Baker R W. Curr. Org. Chem., 2006, 10: 937.
[32] Borie C, Ackermann L, Nechab M. Chem. Soc. Rev., 2016, 45: 1368.
[33] Yue G, Lei K, Hirao H, Zhou J. Angew. Chem. Int. Ed., 2015, 54: 6531.
[34] 乐贵洲(Yue G Z), 黄轩(Huang X), 刘波(Liu B). 有机化学(Chinese Journal of Organic Chemistry), 2013, 33(6): 1167.
[35] 乐贵洲(Yue G Z), 杨立(Yang L), 袁长春(Yuan C C), 杜彪(Du B), 刘波(Liu B). 有机化学(Chinese Journal of Organic Chemistry), 2013, 33(1): 90.
[36] Yue G, Yang L, Yuan C, Jiang X, Liu B. Org. Lett., 2011, 13: 5406.
[37] Yue G, Yang L, Yuan C, Du B, Liu B. Tetrahedron, 2012, 68: 9624.
[38] Yang L, Yue G, Yuan C, Du B, Deng H, Liu B. Synlett, 2014, 25: 2471.
[39] 乐贵洲(Yue G Z). 四川农业大学学报(Journal of Sichuan Agricultural University), 2012, 30(1): 82.
[40] Zhou F, Yang M, Lu X. Org. Lett., 2009, 11: 1405.
[41] Martínez A, García-García P, Fernández-Rodríguez M A, Rodríguez F, Sanz R. Angew. Chem. Int. Ed., 2010, 49: 4633.
[42] Sanjuán A M, Rashid M A, García-García P, Martínez-Cuezva A, Fernández-Rodríguez M A, Rodríguez F, Sanz R. Chem.Eur. J., 2015, 21: 3042.
[43] Tran D N, Cramer N. Angew. Chem. Int. Ed., 2011, 50: 11098.
[44] Campolo D, Gastaldi S, Roussel C, Bertrand M P, Nechab M. Chem. Soc. Rev., 2013, 42: 8434.
[45] Egi M, Shimizu K, Kamiya M, Ota Y, Akai S. Chem. Commun., 2015, 51: 380.
[46] Arif T, Borie C, Tintaru A, Naubron J V, Vanthuyne N, Bertrand M P, Nechab M. Adv. Synth. Catal., 2015, 357: 3611.
[47] Yeom H S, Lee Y, Jeong J, So E, Hwang S, Lee J E, Lee S S, Shin S. Angew. Chem. Int. Ed., 2010, 49: 1611.
[48] Qian D, Zhang J. Chem.Eur. J., 2013, 19: 6984.
[49] Ji K, Zheng Z, Wang Z, Zhang L. Angew. Chem. Int. Ed., 2015, 54: 1245.
[50] Willis M C. Chem. Rev., 2009, 110: 725.
[51] Kundu K, McCullagh J V, Morehead A T. J. Am. Chem. Soc., 2005, 127: 16042.
[52] Natori Y, Anada M, Nakamura S, Nambu H, Hashimoto S. Heterocycles, 2006, 70: 635.
[53] ShintaniR, Yashio K, Nakamura T, Okamoto K, Shimada T, Hayashi T. J. Am. Chem. Soc., 2006, 128: 2772.
[54] Shintani R, Hayashi T. Org. Lett., 2005, 7: 2071.
[55] Shintani R, Takatsu K, Hayashi T. Angew. Chem. Int. Ed., 2007, 46: 3735.
[56] Matsuda T, Makino M, Murakami M. Org. Lett., 2004, 6: 1257.
[57] Matsuda T, Makino M, Murakami M. Angew. Chem. Int. Ed., 2005, 44: 6631.
[58] Matsuda T, Shigeno M, Makino M, Murakami M. Org. Lett., 2006, 8: 3379.
[59] Yu Y N, Xu M H. J. Org. Chem., 2013, 78: 2736.
[60] Minatti A, Zheng X, Buchwald S L. J. Org. Chem., 2007, 72: 9253.
[61] Xie J H, Zhou Q L. Acc. Chem. Res., 2008, 41: 581.
[62] Li X H, Zheng B H, Ding C H, Hou X L. Org. Lett., 2013, 15: 6086.
[63] Yang J, Yoshikai N. J. Am. Chem. Soc., 2014, 136: 16748.
[64] 孙小宇(Sun X Y), 吴劼(Wu J). 有机化学(Chinese Journal of Organic Chemistry), 2006, 26(6): 745.
[65] 姜岚(Jiang L), 李争宁(Li Z N), 赵德峰(Zhao D F). 化学进展(Progress in Chemistry), 2009, 21(6): 1229.
[66] Flanigan D M, Romanov-Michailidis F, White N A, Rovis T. Chem. Rev., 2015, 115: 9307.
[67] Janssen-Müller D, Schedler M, Fleige M, Daniliuc C G, Glorius F. Angew. Chem. Int. Ed., 2015, 54: 12492.
[68] Kerr M S, Rovis T. J. Am. Chem. Soc., 2004, 126: 8876.
[69] Thalji R K, Ellman J A, Bergman R G. J. Am. Chem. Soc., 2004, 126: 7192.
[70] Tran D N, Cramer N. Angew. Chem. Int. Ed., 2010, 49: 8181.
[71] Tran D N, Cramer N. Angew. Chem. Int. Ed., 2013, 52: 10630.
[72] Matsuda T, Watanuki S. Org. Biomol. Chem., 2015, 13: 702.
[73] Soldi C, Lamb K N, Squitieri R A, González-López M, Di Maso M J, Shaw J T. J. Am. Chem. Soc., 2014, 136: 15142.
[74] Albicker M R, Cramer N. Angew. Chem. Int. Ed., 2009, 48: 9139.
[75] Schuster C H, Coombs J R, Kasun Z A, Morken J P. Org. Lett., 2014, 16: 4420.
[76] Martin N, Pierre C, Davi M, Jazzar R, Baudoin O. Chem.Eur. J., 2012, 18: 4480.
[77] Holstein P M, Vogler M, Larini P, Pilet G, Clot E, Baudoin O. ACS Catal., 2015, 5: 4300.
[78] Hu J, Hirao H, Li Y, Zhou J S. Angew. Chem. Int. Ed., 2013, 52: 8676.
[79] Watson M P, Jacobsen E N. J. Am. Chem. Soc., 2008, 130: 12594.
[80] Seiser T, Roth O A, Cramer N. Angew. Chem. Int. Ed., 2009, 48: 6320.
[81] Seiser T, Cramer N. Angew. Chem. Int. Ed., 2010, 49: 10163.
[82] Nishimura T, Guo X X, Hayashi T. Chem. Asian J., 2008, 3: 1505.
[83] Guo X X, Sawano T, Nishimura T, Hayashi T. Tetrahedron: Asymm., 2010, 21: 1730.
[84] Calder E D D, Sutherland A. Org. Lett., 2015, 17: 2514.
[85] Calder E D D, Sutherland A. Synfacts, 2015, 11: 854.
[86] Brekan J A, Reynolds T E, Scheidt K A. J. Am. Chem. Soc., 2010, 132: 1472.
[87] Yuan H, Hu J, Gong Y. Tetrahedron: Asymm., 2013, 24: 699.
[88] Loh C C, Atodiresei I, Enders D. Chem.Eur. J., 2013, 19: 10822.
[89] Loh C C, Hack D, Enders D. Chem. Commun., 2013, 49: 10230.
[90] Loh C C, Chauhan P, Hack D, Lehmann C, Enders D. Adv. Synth. Catal., 2014, 356: 3181.
[91] Yang J W, Hechavarria F M T, List B. J. Am. Chem. Soc., 2005, 127: 15036.
[92] Phillips E M, Wadamoto M, Chan A, Scheidt K A. Angew. Chem. Int. Ed., 2007, 46: 3107.
[93] Li Y, Feng Z, You S L. Chem. Commun., 2008, 44: 2263.
[94] Biswas A, Sarkar S D, Fröhlich R, Studer A. Org. Lett., 2011, 13: 4966.
[95] Belmessieri D, Morrill L C, Simal C, Slawin A M, Smith A D. J. Am. Chem. Soc., 2011, 133: 2714.
[96] Li N, Liu G G, Chen J, Pan F F, Wu B, Wang X W. Eur. J. Org. Chem., 2014, 2014: 2677.
[97] Chua P J, Tan B, Yang L, Zeng X, Zhu D, Zhong G. Chem. Commun., 2010, 46: 7611.
[98] Johnston C P, Kothari A, Sergeieva T, Okovytyy S I, Jackson K E, Paton R S, Smith M D. Nat. Chem., 2015, 7: 171.
[99] Oswald C L, Peterson J A, Lam H W. Org. Lett., 2009, 11: 4504.
[100] Suzuki Y, Yazaki R, Kumagai N, Shibasaki M. Chem. Eur. J., 2011, 17: 11998.
[101] Nishimura T, Ebe Y, Hayashi T. J. Am. Chem. Soc., 2013, 135: 2092.
[102] Nishimura T, Nagamoto M, Ebe Y, Hayashi T. Chem. Sci., 2013, 4: 4499.
[103] Reddy C S, Burns D J, Khan I, Lam H W. Angew. Chem. Int. Ed., 2015, 54: 13975.
[1] Zehuai Mou, Yinjun Wang, Hongyan Xie. Rare-Earth Metal Complexes-Mediated Stereoselective Polymerization of Aromatic Polar Vinyl Monomers [J]. Progress in Chemistry, 2020, 32(12): 1885-1894.
[2] Dongya Bai, Junyao He, Bin Ouyang, Jin Huang, Pu Wang. Biocatalytic Asymmetric Synthesis of Chiral Aryl Alcohols [J]. Progress in Chemistry, 2017, 29(5): 491-501.
[3] Wang Jiandong, Xu Jiaxi. Stereoselective Models for the Electrophilic Addition on the Double Bond Adjacent to A Chiral Centre [J]. Progress in Chemistry, 2016, 28(6): 784-800.
[4] Jiang Kun, Chen Yingchun. The Development of Asymmetric Trienamine Catalysis [J]. Progress in Chemistry, 2015, 27(2/3): 137-145.
[5] Liu Xiang, Pan Zhengguang, Xu Jianhe. Asymmetric Synthesis of Chiral Aryl Vicinal Diols [J]. Progress in Chemistry, 2011, 23(5): 903-913.
[6] . Organocatalytic Asymmetric α-Functionalization of β-Ketoesters [J]. Progress in Chemistry, 2010, 22(09): 1679-1686.
[7] Zhu Yingguang, Di Changwei, Hu Wenhao. Asymmetric Multicomponent Reactions [J]. Progress in Chemistry, 2010, 22(07): 1380-1396.
[8] Li Nan, Liu Weijun, Gong Liuzhu. Asymmetric Organocatalysis [J]. Progress in Chemistry, 2010, 22(07): 1362-1379.
[9] Ma Da-You. Biocatalytic Asymmetric Synthesis of beta-Hydroxy Acid derivatives [J]. Progress in Chemistry, 2008, 20(11): 1687-1693.
[10] Fang Zhao|Tang Ruiren*|Luo Zuowen. Ketene intermediates and their Application in Asymmetric Cycloaddition Reaction [J]. Progress in Chemistry, 2008, 20(10): 1544-1552.
[11] Wang Guixia1 Wang Naixing1** Tang Shi1 Yu Jinlan2 Tang Xinliang2. Asymmetric Synthesis of Chroman Derivatives with Bioactivity [J]. Progress in Chemistry, 2008, 20(04): 518-525.
[12] Xu Jiaxi**. Microwave Irradiation and Selectivities in Organic Reactions [J]. Progress in Chemistry, 2007, 19(05): 700-712.
[13] Linhui Tong Runhua Lu Yoshihisa Inoue Inoue . Asymmetric Photochemistry with Native and Modified Cyclodextrins [J]. Progress in Chemistry, 2006, 18(05): 533-541.
[14] Zhang Zhanjin1,2,Wan Boshun1*,Chen Huilin1. Applications of Chiral Aluminum Catalysts to Asymmetric Synthesis [J]. Progress in Chemistry, 2003, 15(06): 487-.
[15] Li Xiaodong,Lü Shijie,Chan Albert SC. The Application of Modified Heterogeneous Chiral Catalysts in Asymmetric Synthesis [J]. Progress in Chemistry, 2001, 13(01): 33-.