Subscribe to RSS
DOI: 10.1055/a-1577-7850
Development of Synthetic Strategies to Access Optically Pure Feringa’s Motors
Support for this research was provided by the National Natural Science Foundation of China (21901067), from the Ministry of Human Resources and Social Security of China (Starting Grant to Q.L.), and Zhejiang Provincial Natural Science Foundation of China (LY19B040005) (Grant to G.Y.D.).
Abstract
Light-driven unidirectional molecular motors have gained significant attention since the pioneering work by Prof. Ben Feringa in 1999, and they hold great promise as next-generation smart materials. The intrinsic feature of point chirality and the helicity of these molecular motors requires efficient strategies to access their optically pure forms, especially when chirality-sensitive materials are fabricated. In this short review, we summarize synthetic strategies to access optically pure first- and second-generation molecular motors. Three general strategies are discussed: direct asymmetric synthesis, chiral auxiliary methods and chiral separation aided by a resolving agent. We hope that this review will ignite the enthusiasm of synthetic chemists to address very fundamental but unavoidable synthetic questions on chiral-alkene-based molecular motors concerning their large-scale applications.
1 Introduction
2 Synthesis of First-Generation Molecular Motors
2.1 Direct Asymmetric Synthesis of Molecular Motors
2.2 Resolving-Agent-Aided Chiral Resolution of Molecular Motors
3 Synthesis of Second-Generation Molecular Motors
3.1 Direct Asymmetric Synthesis of Molecular Motors
3.2 Chiral Auxiliary Strategy
3.3 Domino Strategy
4 onclusions
Key words
molecular machines - molecular motors - overcrowded alkenes - McMurry reaction - Barton–Kellogg reaction - enantioselectivityPublication History
Received: 28 June 2021
Accepted after revision: 03 August 2021
Accepted Manuscript online:
03 August 2021
Article published online:
22 September 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Feringa BL. Angew. Chem. Int. Ed. 2017; 56: 11060
- 2 Wang JB, Feringa BL. Science 2011; 331: 1429
- 3a Chen JW, Wezenberg SJ, Feringa BL. Chem. Commun. 2016; 52: 6765
- 3b Yue L, Zhang Q, Crespi S, Chen SY, Zhang XK, Xu TY, Ma CS, Zhou SW, Shi ZT, Tian H, Feringa BL, Qu DH. Angew. Chem. Int. Ed. 2021; 60: 16129
- 3c Chen KY, Ivashenko O, Carroll GT, Robertus J, Kistemaker JC. M, London G, Browne WR, Rudolf P, Feringa BL. J. Am. Chem. Soc. 2014; 136: 3219
- 4 van Delden RA, Koumura K, Harada N, Feringa BL. Proc. Natl. Acad. Sci. U.S.A. 2002; 99: 4945
- 5 Pijper D, Feringa BL. Angew. Chem. Int. Ed. 2007; 46: 3693
- 6 Li Q, Fuks G, Moulin E, Maaloum M, Rawiso M, Kulic I, Foy JT, Giuseppone N. Nat. Nanotech. 2015; 10: 161
- 7a García-López V, Chen F, Nilewski LG, Duret G, Aliyan A, Kolomeisky AB, Robinson JT, Wang GF, Pal R, Tour JM. Nature 2017; 548: 567
- 7b Yu JJ, Cao ZQ, Zhang Q, Yang S, Qu DH, Tian H. Chem. Commun. 2016; 52: 12056
- 8a Browne WR, Feringa BL. Nat. Nanotechnol. 2006; 1: 25
- 8b Moulin E, Faour L, Carmona-Vargas CC, Giuseppone N. Adv. Mater. 2020; 32: 1906036
- 8c Dattler D, Fuks G, Heiser J, Moulin E, Perrot A, Yao XY, Giuseppone N. Chem. Rev. 2020; 120: 310
- 8d Shi ZT, Hu YX, Hu ZB, Zhang Q, Chen SY, Chen M, Yu JJ, Yin GQ, Sun HT, Xu L, Li XP, Feringa BL, Yang HB, Tian H, Qu DH. J. Am. Chem. Soc. 2021; 143: 442
- 9a Zhang Q, Qu DH, Tian H, Feringa BL. Matter 2020; 3: 355
- 9b Krause S, Feringa BL. Nat. Rev. Chem. 2020; 4: 550
- 10a Orozco CA, Liu DD, Li YJ, Alemany LB, Pal R, Krishnan S, Tour JM. ACS Appl. Mater. Interfaces 2020; 12: 410
- 10b Galbadage T, Liu DD, Alemany LB, Pal R, Tour JM, Gunasekera RS, Cirillo JD. ACS Nano 2019; 13: 14377
- 10c Liu DD, García-López V, Gunasekera RS, Nilewski LG, Alemany LB, Aliyan A, Jin T, Wang GF, Tour JM, Pal R. ACS Nano 2019; 13: 6813
- 11a Eelkema R, Pollard MM, Vicario J, Katsonis N, Ramon BS, Bastiaansen CW. M, Broer DJ, Feringa BL. Nature 2006; 440: 163
- 11b Orlova T, Lancia F, Loussert C, Iamsaard S, Katsonis N, Brasselet E. Nat. Nanotech. 2018; 13: 304
- 12 Koumura N, Zijlstra RW. J, van Delden RA, Harada N, Feringa BL. Nature 1999; 401: 152
- 13 García-López V, Liu DD, Tour JM. Chem. Rev. 2020; 120: 79
- 14a McMurry JE, Fleming MP. J. Am. Chem. Soc. 1974; 96: 4708
- 14b Fürstner A, Bogdanović B. Angew. Chem. Int. Ed. 1996; 35: 2442
- 15 Evans DA, Ennis MD, Mathre DJ. J. Am. Chem. Soc. 1982; 104: 1737
- 16 ter Wiel MK. J, van Delden RA, Meetsma A, Feringa BL. J. Am. Chem. Soc. 2003; 125: 15076
- 17 Neubauer TM, van Leeuwen T, Zhao DP, Lubbe AS, Kistemaker JC. M, Feringa BL. Org. Lett. 2014; 16: 4220
- 18 van Leeuwen T, Gan J, Kistemaker JC. M, Pizzolato SF, Chang M.-C, Feringa BL. Chem. Eur. J. 2016; 22: 7054
- 19a Koumura N, Geertsema EM, Meetsma A, Feringa BL. J. Am. Chem. Soc. 2000; 122: 12005
- 19b Koumura N, Geertsema EM, Gelder van M B, Meetsma A, Feringa BL. J. Am. Chem. Soc. 2002; 124: 5037
- 20a Barton DH. R, Smith EH, Willis BJ. J. Chem. Soc. D 1970; 1225
- 20b Buter J, Wassenaar S, Kellogg RM. J. Org. Chem. 1972; 37: 4045
- 21 Pijper TC, Pijper D, Pollard MM, Dumur F, Davey SG, Meetsma A, Feringa BL. J. Org. Chem. 2010; 75: 825
- 22 van Leeuwen T, Danowski W, Otten E, Wezenberg SJ, Feringa BL. J. Org. Chem. 2017; 82: 5027
- 23 Li Q, Foy JT, Colard-Itté J.-R, Goujon A, Dattler D, Fuks G, Moulin E, Giuseppone N. Tetrahedron 2017; 73: 4874
- 24a Tietze LF. Chem. Rev. 1996; 96: 115
- 24b Tietze LF, Waldecker B, Ganapathy D, Eichhorst C, Lenzer T, Oum K, Reichmann SO, Stalke D. Angew. Chem. Int. Ed. 2015; 54: 10317
- 25a Xue F, Zhao J, Hor TS. A, Hayashi T. J. Am. Chem. Soc. 2015; 137: 3189
- 25b Wang JC, Dong Z, Yang C, Dong GB. Nat. Chem. 2019; 11: 1106
- 26 Tietze LF, Düfert A, Lotz F, Sölter L, Oum K, Lenzer T, Beck T, Herbst-Irmer R. J. Am. Chem. Soc. 2009; 131: 17879
- 27 Liu HQ, El-Salfiti M, Lautens M. Angew. Chem. Int. Ed. 2012; 51: 9846
- 28 Heard AW, Goldup SM. ACS Cent. Sci. 2020; 6: 117