机械手性轮烷研究进展

doi:10.6023/cjoc202504033

摘要/Abstract

机械手性轮烷作为机械互锁分子的重要分支,凭借机械键诱导的独特立体化学特性,在分子机器与不对称催化等领域展现出广阔应用前景. 根据组件的对称性特征,轮烷的机械手性主要分为机械面手性、机械轴手性与机械点手性三类. 本文基于非手性组件的对称面分析,组合各种类型的大环和轴体,阐述了这三类机械手性的特征. 当前,机械手性轮烷的制备主要是基于手性池和手性辅基的非对映选择性合成策略,基于手性催化剂的对映选择性催化合成机械面手性和机械点手性轮烷也有少量报道. 按轮烷的机械手性分类,本文从合成方法上对该领域现状和未来发展进行了总结与展望. 本文还简要介绍了机械手性轮烷的应用.

关键词: 轮烷, 机械面手性, 机械轴手性, 对称面, 不对称合成

Mechanically chiral rotaxanes, as a critical subclass of mechanically interlocked molecules (MIMs), demonstrate broad application prospects in molecular machines and asymmetric catalysis due to their unique stereochemical properties induced by mechanical bonds. Based on the symmetry feature of their components, mechanical chirality of rotaxanes is classified into three categories: mechanically planar chirality, mechanically axial chirality, and mechanical point-chirality. The stereochemical features of these three types are elucidated by analyzing the symmetry planes of each achiral macrocycle and axle, and then combining these two components. Currently, the preparation of mechanically chiral rotaxanes mainly relies on diastereoselective strategies employing chiral pools or chiral auxiliaries. A limited number of catalytic enantioselective synthesis of mechanically planar chiral and mechanically point-chiral rotaxanes have also been reported. This review systematically summarizes the current status and future directions in the field, categorized by the types of rotaxane chirality and their corresponding synthetic strategies. Application of mechanically chiral rotaxanes is also briefly introduced.

Key words: rotaxane, mechanically planar chirality, mechanically axial chirality, symmetry plane, asymmetric synthesis

引用此文

朱瑞卿, 朱婷, 王超, 宗利利. 机械手性轮烷研究进展[J]. 有机化学, doi: 10.6023/cjoc202504033.

Zhu Ruiqing, Zhu Ting, Wang Chao, Zong Lili. Research Progress in Mechanically Chiral Rotaxanes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202504033.

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

分享此文

参考文献

[1] Bruns, C. J.; Stoddart, J. F. The Nature of the Mechanical Bond: From Molecules to Machines; John Wiley & Sons: Hoboken, NJ, 2017.
[2] (a) Yin, X. X.; Li, J. J.; Zhuo K. X.; Mou, W. X.; Huang, L. L.; Chen, J. Z.; Lin, S. L. Acta Chim. Sinica 2024, 82, 790 (in Chinese). (尹晓璇, 李进杰, 禚可欣, 牟蔚鑫, 黄灵丽, 陈健壮, 林绍梁, 化学学报, 2024, 82, 790.)
(b) Li, D. X.; Xu, X.; Song, J. G.; Liang, S. T.; Fu, Y.; Lu, X. H.; Zou, Y. P. Acta Chim. Sinica 2023, 81, 1500 (in Chinese). (李东旭, 徐翔, 宋佳鸽, 梁松挺, 付予昂, 路新慧, 邹应萍, 化学学报 2023, 81, 1500.)
(c) Sun, C. L.; Teng, K. X.; Niu, L. Y.; Chen, Y. Z.; Yang, Q. Z. Acta Chim. Sinica, 2018, 76, 779 (in Chinese). (孙才力, 滕坤旭, 牛丽亚, 陈玉哲, 杨清正, 化学学报, 2018, 76, 779.)
(d) Wang, Y. F.; Liu, H. H.; Zhu, X. Y. Acta Chimica Sinica, 2020, 78, 746 (in Chinese). (王友付, 刘航海, 朱新远, 化学学报, 2020, 78, 746.)
[3] (a) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492.
(b) Crittall, M. R.; Rzepa, H. S.; Carbery, D. R. Org. Lett. 2011, 13, 1250.
[4] (a) Jamieson, E. M. G.; Modicom, F.; Goldup, S. M. Chem. Soc. Rev. 2018, 47, 5266.
(b) Evans, N. H.; Chem. Eur. J. 2018, 24, 3101.
(c) Maynard, J. R. J.; Goldup, S. M. Chem 2020, 6, 1914.
(d) Nakazono, K.; Takata, T. Symmetry 2020, 12, 144.
(e) Tang, M.; Yang, X. Eur. J. Org. Chem. 2023, 26, e202300738.
(f) Zhou, X. H.; Wang, W. Sci Sin Chim. 2023, 53, 2460 (in Chinese). (周肖华, 王威, 中国科学（化学）, 2023, 53, 2460.)
[5] Yamamoto, C.; Okamoto, Y.; Schmidt, T.; Jäger, R.; Vögtle, F. J. Am. Chem. Soc. 1997, 119, 10547.
[6] Tachibana, Y.; Kihara, N.; Takata, T. J. Am. Chem. Soc. 2004, 126, 3438.
[7] (a) Krajnc, M.; Niemeyer, J. Beilstein J. Org. Chem. 2022, 18, 508.
(b) Martinez-Cuezva, A.; Saura-Sanmartin, A.; Alajarin, M.; Berna, J. ACS Catal. 2020, 10, 7719.
(c) Wang, Q.-Q. Supramolecular Catalysis Using Organic Macrocycles, Eds.: Liu, Y.; Chen, Y.; Zhang, H.-Y., Springer, Singapore, 2019, pp. 1-47.
[8] Bordoli, R. J.; Goldup, S. M. J. Am. Chem. Soc. 2014, 136, 4817.
[9] Maynard, J. R. J; Gallagher, P, Lozano, D; Butler, P; Goldup, S. M. Nat. Chem. 2022, 14, 1038.
[10] (a) Manna, P. L.; Talotta, C.; Gaeta, C.; Soriente, A.; Rosa, M. D.; Neri, P. J. Org. Chem. 2017, 82, 8973.
(b) Bazzoni, M.; Andreoni, L.; Silvi, S.; Credi, A.; Cera, G.; Secchi, A.; Arduini, A. Chem. Sci. 2021, 12, 6419.
(c) Cera, G.; Arduini, A.; Secchi, A.; Credi, A.; Silvi, S. Chem. Rec. 2021, 21, 1161.
(d) Andreoni, L.; Bonati, F.C.; Groppi, J.; Balestri, D.; Cera, G.; Credi, A.; Secchi, A.; Silvi, S. Chem. Commun. 2023, 59, 4970.
[11] Savoini, A.; Gallagher, R. P.; Saady A.; Goldup, S. M. J. Am. Chem. Soc. 2024, 146, 8472.
[12] (a) Alvarez-Pérez, M.; Goldup, S. M.; Leigh, D. A.; Slawin, A. M. Z. J. Am. Chem. Soc. 2008, 130, 1836.
(b) Cakmak, Y.; Erbas-Cakmak, S.; Leigh, D.A. J. Am. Chem. Soc. 2016, 138, 1749.
[13] Goldup, S. M. Acc. Chem. Res. 2024, 57, 1696.
[14] Mochizuki, Y.; Ikeyatsu, K.; Mutoh, Y.; Hosoya, S.; Saito, S. Org. Lett. 2017, 19, 4347.
[15] Corra, S.; Vet, C.; Groppi, J.; Rosa, L. M.; Silvi, S.; Baroncini, M.; Credi, A. J. Am. Chem. Soc. 2019, 141, 9129.
[16] (a) Han, X.; Liu, G.; Liu. S.; Yin. J. Org. Biomol. Chem. 2016. 14, 10331.
(b) Denis, M.; Goldup, S. M. Nat. Rev. Chem. 2017, 1, 61.
(c) Shahraki, B. T.; Maghsoudi, S.; Fatahi, Y.; Rabiee, N.; Bahadorikhalili, S.; Dinarvand, R.; Bagherzadeh, M.; Verpoort, F. Coord. Chem. Rev. 2020, 423, 213484.
[17] Johnston, A. G.; Leigh, D. A.; Murphy, A.; Smart, J.P.; Deegan, M. D. J. Am. Chem. Soc. 1996, 118, 10662.
[18] Fujimura, K.; Ueda, Y.; Yamaoka, Y.; Takasu, K.; Kawabata, T. Angew. Chem. Int. Ed. 2023, 62, e202303078.
[19] Wisner, J. A.; Beer, P. D.; Drew, M. G. B.; Sambrook, M. R. J. Am. Chem. Soc. 2002, 124, 12469.
[20] Tachibana, Y.; Kawasaki, H.; Kihara, N.; Takata, T. J. Org. Chem. 2006, 71, 5093.
[21] Crowley, J. D.; Goldup, S. M.; Lee, A.-L.; Leigh, D. A.; McBurney, R. T. Chem. Soc. Rev. 2009, 38, 1530.
[22] (a) Aucagne, V.; Hanni, K. D.; Leigh, D. A.; Lusby, P. J.; Walker, D. B. J. Am. Chem. Soc. 2006, 128, 2186.
(b) Aucagne, V.; Berná, J.; Crowley, J. D.; Goldup, S. M.; Hänni, K. D.; Leigh, D. A.; Lusby, P. J.; Ronaldson, V. E.; Slawin, A. M. Z.; Viterisi, A.; Walker, D. B. J. Am. Chem. Soc. 2007, 129, 11950.
[23] Anghel, C. C.; Cucuiet, A. T.; Hădade, D. N.; Grosu, I. Beilstein J. Org. Chem. 2023, 19, 1776.
[24] (a) De Bo, G.; Dolphijn, G.; McTernan, C. T.; Leigh, D. A. J. Am. Chem. Soc. 2017, 139, 8455.
(b) Fielden, S. D. P.; Leigh, D. A.; McTernan, C. T.; Pérez-Saavedra, B.; Vitorica-Yrezabal, I. J. J. Am. Chem. Soc. 2018, 140, 6049.
(c) Fielden, D. P. S. ChemSystemsChem 2024, 6, e202300048.
[25] Tian, C.; Fielden, S. D. P.; Whitehead, G. F. S.; Vitorica-Yrezabal, I. J.; Leigh, D. A. Nat. Commun. 2020, 11, 744.
[26] Jinks, M. A.; de Juan, A.; Denis, M.; Fletcher, C. J.; Galli, M.; Jamieson, E. M. G.; Modicom, F.; Zhang, Z.; Goldup, S. M. Angew. Chem. Int. Ed. 2018, 57, 14806.
[27] Zhang, S.; Rodríguez-Rubio, A.; Saady, A.; Tizzard, J. G.; Goldup, S. M. Chem 2023, 9, 1195.
[28] de Juan, A.; Lozano, D.; Heard, A. W.; Jinks, M. A.; Suarez, J. M.; Tizzard, G. J.; Goldup, S. M. Nat. Chem. 2022, 14, 179.
[29] Saura-Sanmartin, A. Chem. Eur. J. 2024, 30, e202304025.
[30] Tian, C.; Fielden, S. D. P.; Pérez-Saavedra, B.; Vitorica-Yrezabal, I. J.; Leigh, D. A. J. Am. Chem. Soc. 2020, 142, 9803.
[31] Gallagher, R. P.; Savoini, A.; Abed, S.; Maynard, R.J. J.; Butler, W. V. P.; Tizzard, J. G.; Goldup, S. M. J. Am. Chem. Soc. 2024, 146, 9134.
[32] Makita, Y.; Kihara, N.; Nakakoji, N.; Takata, T.; Inagaki, S.; Yamamoto, C.; Okamoto, Y. Chem. Lett. 2007, 36, 162.
[33] Imayoshi, A.; Lakshmi, B. V.; Ueda, Y.; Yoshimura, T.; Matayoshi, A.; Furuta, T.; Kawabata, T. Nat. Commun. 2021, 12, 404.
[34] Li, M.; Chia, X.; Tian, C.; Zhu, Y. Chem 2022, 8, 2843.
[35] Heard, A. W.; Goldup, S. M. Chem 2020, 6, 994.
[36] Puigcerver, J.; Marin-Luna, M.; Iglesias-Sigüenza, J.; Alajarin, M.; Martinez-Cuezva, A.; Berna, J. J. Am. Chem. Soc. 2024, 146, 2882.
[37] Rodríguez-Rubio, A.; Savoini, A.; Modicom, F.; Butler, P.; Goldup, S. M. J. Am. Chem. Soc. 2022, 144, 11927.