Subscribe to RSS
DOI: 10.1055/a-2513-2141
Supramolecular Chemistry: An Enabling Tool for Asymmetric Catalysis

Dedicated to the memory and achievements of the late Prof. Dervilla M. X. Donnelly, a trailblazer of Irish chemistry
Abstract
Asymmetric synthesis and supramolecular chemistry are cornerstones of modern organic chemistry. The combination of both fields to develop new approaches to enantioselective catalysis has gained considerable momentum in recent years. Herein, we highlight some of the advantages offered by various supramolecular architectures over conventional chiral catalysts and reflect on obstacles that currently limit widespread use of supramolecular tools in asymmetric synthesis.
1 Introduction
2 Discussion
2.1 Macrocycles
2.2 Surfactants
2.3 Metal-Organic Cages and Frameworks
2.4 Covalent Organic Frameworks
2.5 DNA
2.6 Mechanically Interlocked Molecules
3 Summary and Outlook
Key words
asymmetric catalysis - supramolecular chemistry - macrocycle - metal-organic assemblies - host–guest systems - mechanically interlocked molecules - micellesPublication History
Received: 03 December 2024
Accepted after revision: 09 January 2025
Accepted Manuscript online:
09 January 2025
Article published online:
19 February 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Pedersen CJ. J. Am. Chem. Soc. 1967; 89: 7017
- 2 Yu J, Qi D, Li J. Commun. Chem. 2020; 3: 189
- 3 He Q, Vargas-Zúñiga GI, Kim SH, Kim SK, Sessler JL. Chem. Rev. 2019; 119: 9753
- 4 Teixeira J, Tiritan ME, Pinto MM. M, Fernandes C. Molecules 2019; 24: 865
- 5 Zhang Z, Shao Y, Tang J, Jiang J, Wang L, Li S. Green Synth. Catal. 2021; 2: 156
- 6 Durmaz M, Halay E, Bozkurt S. Beilstein J. Org. Chem. 2018; 14: 1389
- 7 Macaev F, Boldescu V. Symmetry 2015; 7: 1699
- 8 Nagata Y, Shimada Y, Nishikawa T, Takeda R, Uno M, Ogoshi T, Suginome M. Synlett 2018; 29: 2167
- 9 Morimoto M, Bierschenk SM, Xia KT, Bergman RG, Raymond KN, Toste FD. Nat. Catal. 2020; 3: 969
- 10 Tao JJ, Tang JD, Hong T, Ye JW, Chen JY, Xie C, Zhang Z, Li S. ACS Omega 2021; 6: 35093
- 11 Ouyang G, He Y, Li Y, Xiang J, Fan Q. Angew. Chem. Int. Ed. 2015; 54: 4334
- 12 Luo Y, Ouyang G, Tang Y, He YM, Fan QH. J. Org. Chem. 2020; 85: 8176
- 13 Nagayama S, Kobayashi S. J. Am. Chem. Soc. 2000; 122: 11531
- 14 Nemcsok T, Rapi Z, Bagi P, Guan YH, Orbán I, Keglevich G, Bakó P. Tetrahedron 2020; 76: 130965
- 15 Guo H, Zhang L, Zhou H, Meng W, Ao Y, Wang D, Wang Q. Angew. Chem. 2020; 132: 2645
- 16 Zhang XC, Hu YH, Chen CF, Fang Q, Yang LY, Lu YB, Xie LJ, Wu J, Li S, Fang W. Chem. Sci. 2016; 7: 4294
- 17 Tao JJ, Tang JD, Hong T, Ye JW, Chen JY, Xie C, Zhang Z, Li S. ACS Omega 2021; 6: 35093
- 18 Yoo C, Dodge HM, Miller AJ. M. Chem. Commun. 2019; 55: 5047
- 19 Zhang P, Tugny C, Meijide Suárez J, Guitet M, Derat E, Vanthuyne N, Zhang Y, Bistri O, Mouriès-Mansuy V, Ménand M, Roland S, Fensterbank L, Sollogoub M. Chem 2017; 3: 174
- 20 Guitet M, Zhang P, Marcelo F, Tugny C, Jiménez-Barbero J, Buriez O, Amatore C, Mouriès-Mansuy V, Goddard JP, Fensterbank L, Zhang Y, Roland S, Ménand M, Sollogoub M. Angew. Chem. Int. Ed. 2013; 52: 7213
- 21 Xu G, Leloux S, Zhang P, Meijide Suárez J, Zhang Y, Derat E, Ménand M, Bistri-Aslanoff O, Roland S, Leyssens T, Riant O, Sollogoub M. Angew. Chem. Int. Ed. 2020; 59: 7591
- 22 Hirano K, Takano S, Tsukuda T. Chem. Commun. 2019; 55: 15033
- 23 Yang C, Ke C, Liang W, Fukuhara G, Mori T, Liu Y, Inoue Y. J. Am. Chem. Soc. 2011; 133: 13786
- 24 Wang Q, Liang W, Wei X, Wu W, Inoue Y, Yang C, Liu Y. Org. Lett. 2020; 22: 9757
- 25 Wei X, Ji J, Nie Y, Tang L, Rao M, Wang X, Wu W, Su D, Zhong Z, Yang C. Nat. Protoc. 2022; 17: 2494
- 26 Ji J, Wei X, Wu W, Yang C. Acc. Chem. Res. 2023; 56: 1896
- 27 Wu Y, Aslani S, Han H, Tang C, Wu G, Li X, Wu H, Stern CL, Guo QH, Qiu Y, Chen AX. Y, Jiao Y, Zhang R, David AH. G, Armstrong DW, Fraser StoddartJ. Nat. Synth. 2024; 3: 698
- 28 Larsen D, Beeren SR. Chem. Sci. 2019; 10: 9981
- 29 Erichsen A, Peters GH. J, Beeren SR. J. Am. Chem. Soc. 2023; 145: 4882
- 30 Gopalsamuthiram V, Wulff WD. J. Am. Chem. Soc. 2004; 126: 13936
- 31 Gopalsamuthiram V, Predeus AV, Huang RH, Wulff WD. J. Am. Chem. Soc. 2009; 131: 18018
- 32 Guérineau V, Rollet M, Viel S, Lepoittevin B, Costa L, Saint-Aguet P, Laurent R, Roger P, Gigmes D, Martini C, Huc V. Nat. Commun. 2019; 10: 113
- 33 Sachdeva G, Vaya D, Srivastava CM, Kumar A, Rawat V, Singh M, Verma M, Rawat P, Rao GK. Coord. Chem. Rev. 2022; 472: 214791
- 34 Mandadapu V, Day AI, Ghanem A. Chirality 2014; 26: 712
- 35 Lai Z, Zhao T, Sessler JL, He Q. Coord. Chem. Rev. 2020; 425: 213528
- 36 Chen CF, Han Y. Acc. Chem. Res. 2018; 51: 2093
- 37 Shi Q, Wang X, Liu B, Qiao P, Li J, Wang L. Chem. Commun. 2021; 57: 12379
- 38 Tong S, Li JT, Liang DD, Zhang YE, Feng QY, Zhang X, Zhu J, Wang MX. J. Am. Chem. Soc. 2020; 142: 14432
- 39 Herbert SA, Van Laeren LJ, Castell DC, Arnott GE. Beilstein J. Org. Chem. 2014; 10: 2751
- 40 Bonaccorso C, Brancatelli G, Ballistreri FP, Geremia S, Pappalardo A, Tomaselli GA, Toscano RM, Sciotto D. Dalton Trans. 2014; 43: 2183
- 41 Gröger H, Gallou F, Lipshutz BH. Chem. Rev. 2023; 123: 5262
- 42 Virdi JK, Dusunge A, Handa S. JACS Au 2024; 4: 301
- 43 Lorenzetto T, Fabris F, Scarso A. Curr. Opin. Colloid Interface Sci. 2023; 64: 101689
- 44 La Sorella G, Strukul G, Scarso A. Green Chem. 2015; 17: 644
- 45 Nagtode VS, Cardoza C, Yasin HK. A, Mali SN, Tambe SM, Roy P, Singh K, Goel A, Amin PD, Thorat BR, Cruz JN, Pratap AP. ACS Omega 2023; 8: 11674
- 46 Xiong Z, Zhou L, Wang J, Tian M, Fan Y, Wang Y. Curr. Opin. Colloid Interface Sci. 2024; 73: 101842
- 47 Fox RJ, Bailey JD, Obligacion JV, Borlinghaus N, Braje WM, Li X, Mukherjee S, Schoen A, Towne TB, Vukelić S. Org. Process Res. Dev. 2024; 28: 978
- 48 Lipshutz BH. Green Chem. 2023; 26: 739
- 49 Cortes-Clerget M, Yu J, Kincaid JR. A, Walde P, Gallou F, Lipshutz BH. Chem. Sci. 2021; 12: 4237
- 50 Lipshutz BH, Ghorai S. Org. Lett. 2012; 14: 422
- 51 Li J, Lin Z, Huang Q, Wang Q, Tang L, Zhu J, Deng J. Green Chem. 2017; 19: 5367
- 52 Liang X, Gui Y, Li K, Li J, Zha Z, Shi L, Wang Z. Chem. Commun. 2020; 56: 11118
- 53 Lipshutz BH, Isley NA, Moser R, Ghorai S, Leuser H, Taft BR. Adv. Synth. Catal. 2012; 354: 3175
- 54 Ahmed E, Cho J, Friedmann L, Jang SS, Weck M. JACS Au 2022; 2: 2316
- 55 Shairgojray BA, Dar AA, Bhat BA. Catal. Commun. 2016; 83: 58
- 56 Xu L, Zhou L, Li YX, Gao RT, Chen Z, Liu N, Wu ZQ. Nat. Commun. 2023; 14: 7287
- 57 Cavarzan A, Bianchini G, Sgarbossa P, Lefort L, Gladiali S, Scarso A, Strukul G. Chem. Eur. J. 2009; 15: 7930
- 58 Yusuf VF, Malek NI, Kailasa SK. ACS Omega 2022; 7: 44507
- 59 Berijani K, Chang LM, Gu ZG. Coord. Chem. Rev. 2023; 474: 214852
- 60 Zhang D, Ronson TK, Zou YQ, Nitschke JR. Nat. Rev. Chem. 2021; 5: 168
- 61 Sepehrpour H, Fu W, Sun Y, Stang PJ. J. Am. Chem. Soc. 2019; 141: 14005
- 62 Ashbridge Z, Reek JN. H. Nat. Synth. 2024; 3: 1197
- 63 Furukawa H, Cordova KE, O’Keeffe M, Yaghi OM. Science 2013; 341: 1230444
- 64 Pilgrim BS, Champness NR. ChemPlusChem 2020; 85: 1842
- 65 Young RJ, Huxley MT, Pardo E, Champness NR, Sumby CJ, Doonan CJ. Chem. Sci. 2020; 11: 4031
- 66 Chen X, Jiang H, Li X, Hou B, Gong W, Wu X, Han X, Zheng F, Liu Y, Jiang J, Cui Y. Angew. Chem. 2019; 131: 14890
- 67 Jiao J, Tan C, Li Z, Liu Y, Han X, Cui Y. J. Am. Chem. Soc. 2018; 140: 2251
- 68 Begato F, Licini G, Zonta C. Angew. Chem. Int. Ed. 2023; 62: e202311153
- 69 Li Y, He J, Lu G, Wang C, Fu M, Deng J, Yang F, Jiang D, Chen X, Yu Z, Liu Y, Yu C, Cui Y. Nat. Commun. 2024; 15: 7044
- 70 Bierschenk SM, Pan JY, Settineri NS, Warzok U, Bergman RG, Raymond KN, Toste FD. J. Am. Chem. Soc. 2022; 144: 11425
- 71 Seo SL, Whank D, Lee H, Jun SI, Oh J, Jeon YJ, Kim K. Nature 2000; 404: 982
- 72 Antil N, Akhtar N, Newar R, Begum W, Kumar A, Chauhan M, Manna K. ACS Catal. 2021; 11: 10450
- 73 García-Simón C, Gramage-Doria R, Raoufmoghaddam S, Parella T, Costas M, Ribas X, Reek JN. H. J. Am. Chem. Soc. 2015; 137: 2680
- 74 Dybtsev DN, Bryliakov KP. Coord. Chem. Rev. 2021; 437: 213845
- 75 Ghosh A, Slappendel L, Nguyen BN. T, Von Krbek LK. S, Ronson TK, Castilla AM, Nitschke JR. J. Am. Chem. Soc. 2022; 145: 3828
- 76 Black MR, Bhattacharyya S, Argent SP, Pilgrim BS. J. Am. Chem. Soc. 2024; 146: 28233
- 77 Dong J, Wee V, Zhao D. Nat. Mater. 2022; 21: 1334
- 78 Howarth AJ, Liu Y, Li P, Li Z, Wang TC, Hupp JT, Farha OK. Nat. Rev. Mater. 2016; 1: 15018
- 79 Pullen S, Clever GH. Acc. Chem. Res. 2018; 51: 3052
- 80 Huang YB, Liang J, Wang XS, Cao R. Chem. Soc. Rev. 2017; 46: 126
- 81 Song F, Wang C, Lin W. Chem. Commun. 2011; 47: 8256
- 82 Ueda Y, Ito H, Fujita D, Fujita M. J. Am. Chem. Soc. 2017; 139: 6090
- 83 Biemmi E, Christian S, Stock N, Bein T. Microporous Mesoporous Mater. 2009; 117: 111
- 84 Chalati T, Horcajada P, Gref R, Couvreur P, Serre C. J. Mater. Chem. 2011; 21: 2220
- 85 Stock N, Biswas S. Chem. Rev. 2012; 112: 933
- 86 Millange F, El Osta R, Medina ME, Walton RI. CrystEngComm 2011; 13: 103
- 87 Brightwell DF, Samanta K, Muldoon J, Fleming PC, Ortin Y, Mardiana L, Waddell PG, Hall MJ, Clark ER, Fantuzzi F, Palma A. ChemistryEurope 2024; 3: e202400050
- 88 Rosen AS, Fung V, Huck P, O’Donnell CT, Horton MK, Truhlar DG, Persson KA, Notestein JM, Snurr RQ. npj Comput. Mater. 2022; 8: 112
- 89 Tarzia A, Lewis J, Jelfs K. Angew. Chem. Int. Ed. 2021; 60: 20879
- 90 Geng K, He T, Liu R, Dalapati S, Tan KT, Li Z, Tao S, Gong Y, Jiang Q, Jiang D. Chem. Rev. 2020; 120: 8814
- 91 Feng X, Ding X, Jiang D. Chem. Soc. Rev. 2012; 41: 6010
- 92 Ma H.-C, Zou J, Li X.-T, Chen G.-J, Dong Y.-B. Chem. Eur. J. 2020; 26: 13754
- 93 Zhang H, Lou LL, Yu K, Liu S. Small 2021; 17: 2005686
- 94 Dong YB, Wang JC, Kan X, Shang JY, Qiao H. J. Am. Chem. Soc. 2020; 142: 16915
- 95 Li F, Kan JL, Yao BJ, Dong Y.-B. Angew. Chem. Int. Ed. 2022; 61: e202115044
- 96 Han X, Zhang J, Huang J, Wu X, Yuan D, Liu Y, Cui Y. Nat. Commun. 2018; 9: 1294
- 97 Ma HC, Sun YN, Chen GJ, Dong Y.-B. Chem. Sci. 2022; 13: 1906
- 98 Côte AP, Benin AI, Ockwig BnW, O’Keeffe M, Matzger AJ, Yaghi MO. Science 2005; 310: 1166
- 99 Xu H, Chen X, Gao J, Lin J, Addicoat M, Irle S, Jiang D. Chem. Commun. 2014; 50: 1292
- 100 Wang JC, Liu CX, Kan X, Wu XW, Kan JL, Dong Y.-B. Green Chem. 2020; 22: 1150
- 101 Roelfes G, Feringa BL. Angew. Chem. Int. Ed. 2005; 44: 3230
- 102 García-Fernández A, Megens RP, Villarino L, Roelfes G. J. Am. Chem. Soc. 2016; 138: 16308
- 103 Yum JH, Sugiyama H, Park S. Chem. Rec. 2022; 22: e202100333
- 104 Boersma AJ, Megens RP, Feringa BL, Roelfes G. Chem. Soc. Rev. 2010; 39: 2083
- 105 Silverman SK. Angew. Chem. Int. Ed. 2010; 49: 7180
- 106 Mansot J, Aubert S, Duchemin N, Vasseur JJ, Arseniyadis S, Smietana M. Chem. Sci. 2019; 10: 2875
- 107 Aubert S, Duchemin N, Zhang J.-L, Smietana M, Arseniyadis S. In Topics in Enantioselective Catalysis, Vol. 9 . Kadisch KM, Guilard R. World Scientific; Singapore: 2022: 1-30
- 108 Sheng J, Li Z, Koh KK. Y, Shi Q, Foo A, Tan PM. L, Kha TK, Wang X, Fang L, Zhu RY. J. Am. Chem. Soc. 2024; 146: 16531
- 109 Boersma AJ, Klijn JE, Feringa BL, Roelfes G. J. Am. Chem. Soc. 2008; 130: 11783
- 110 Cheng Y, Cheng M, Hao J, Jia G, Li C. ChemBioChem 2018; 19: 2233
- 111 Colas Y, Ménage S, Marchi-Delapierre C, Spinelli N. ChemCatChem 2024; 16: e202300914
- 112 Draksharapu A, Boersma AJ, Leising M, Meetsma A, Browne WR, Roelfes G. Dalton Trans. 2015; 44: 3647
- 113 Guo J, Wang D, Pantatosaki E, Kuang H, Papadopoulos GK, Tsapatsis M, Kokkoli E. JACS Au 2022; 2: 483
- 114 Benedetti E, Duchemin N, Bethge L, Vonhoff S, Klussmann S, Vasseur JJ, Cossy J, Smietana M, Arseniyadis S. Chem. Commun. 2015; 51: 6076
- 115 Park S, Ikehata K, Sugiyama H. Biomater. Sci. 2013; 1: 1034
- 116 Pal M, Musib D, Pal M, Rana G, Bag G, Dutta S, Roy M. Org. Biomol. Chem. 2021; 19: 5072
- 117 Hao J, Miao W, Cheng Y, Lu S, Jia G, Li C. ACS Catal. 2020; 10: 6561
- 118 Tachibana Y, Kihara N, Takata T. J. Am. Chem. Soc. 2004; 126: 3438
- 119 Mitra R, Zhu H, Grimme S, Niemeyer J. Angew. Chem. Int. Ed. 2017; 56: 11456
- 120 Evans NH. Chem. Eur. J. 2018; 24: 3101
- 121 Jamieson EM. G, Modicom F, Goldup SM. Chem. Soc. Rev. 2018; 47: 5266
- 122 Hoekman S, Kitching MO, Leigh DA, Papmeyer M, Roke D. J. Am. Chem. Soc. 2015; 137: 7656
- 123 Blanco V, Leigh DA, Marcos V, Morales-Serna JA, Nussbaumer AL. J. Am. Chem. Soc. 2014; 136: 4905
- 124 Jansen D, Gramüller J, Niemeyer F, Schaller T, Letzel MC, Grimme S, Zhu H, Gschwind RM, Niemeyer J. Chem. Sci. 2020; 11: 4381
- 125 Kauerhof D, Riebe J, Vonnemann CJ, Thiele M, Jansen D, Niemeyer J. Chem. Commun. 2024; 60: 2393
- 126 Ishiwari F, Nakazono K, Koyama Y, Takata T. Angew. Chem. 2017; 129: 15054
- 127 Heard AW, Goldup SM. Chem 2020; 6: 994
- 128 Goldup SM. Acc. Chem. Res. 2024; 57: 1696
- 129 Hattori G, Hori T, Miyake Y, Nishibayashi Y. J. Am. Chem. Soc. 2007; 129: 12930
- 130 Scholtes JF. Trapp O. Organometallics 2019; 38: 3955
- 131 Puigcerver J, Marin-Luna M, Iglesias-Sigüenza J, Alajarin M, Martinez-Cuezva A, Berna J. J. Am. Chem. Soc. 2024; 146: 2882
- 132 Calles M, Puigcerver J, Alonso DA, Alajarin M, Martinez-Cuezva A, Berna J. Chem. Sci. 2020; 11: 3629
- 133 Leforestier B, Gyton MR, Chaplin AB. Angew. Chem. Int. Ed. 2020; 59: 23500