茚及其衍生物的催化不对称合成

何桥; 殷中琼; 陈华保; 张祖民; 王显祥; 乐贵洲

doi:10.7536/PC160102

化学进展 ›› 2016, Vol. 28 ›› Issue (6) :801-813 DOI: 10.7536/PC160102

综述与评论

扫码查看或转发全文

茚及其衍生物的催化不对称合成

^1,2*

作者信息 +

Catalytic Asymmetric Syntheses of Indenes and Their Derivatives

He Qiao², Yin Zhongqiong³, Chen Huabao², Zhang Zumin¹, Wang Xianxiang¹, Yue Guizhou^1,2*

Author information +

文章历史 +

摘要

茚及其衍生物广泛存在于自然界中,其中多官能团化的茚类化合物大多具有重要的生物活性,因而非常具有成为药物的先导化合物的潜力。特别是茚类化合物的不对称合成吸引了有机化学家们的广泛关注,最近有许多相应的合成方法研究被报道,包括外消旋体拆分、手性辅基及底物诱导的合成和手性催化合成等。本文总结了茚及其衍生物的催化不对称合成研究进展,重点介绍过渡金属及有机小分子不对称催化反应,并对该领域的研究前景进行了展望。

Abstract

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

Graphical abstract

关键词

茚 / 茚酮 / 氢化茚 / 茚醇 / 立体选择性 / 不对称合成

Key words

indene / indanone / indane / indanol / stereoselectivity / asymmetric synthesis

引用本文

引用格式 ▾

何桥, 殷中琼, 陈华保, 张祖民, 王显祥, 乐贵洲. 茚及其衍生物的催化不对称合成[J]. 化学进展, 2016, 28(6): 801-813 DOI:10.7536/PC160102

He Qiao, Yin Zhongqiong, Chen Huabao, Zhang Zumin, Wang Xianxiang, Yue Guizhou. Catalytic Asymmetric Syntheses of Indenes and Their Derivatives[J]. Progress in Chemistry, 2016, 28(6): 801-813 DOI:10.7536/PC160102

登录浏览全文

4963

注册一个新账户忘记密码

参考文献

原文顺序 | 出版日期 | 本文引用

[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.