1. Noyori, R. Asymmetric Catalysis: Science and Opportunities (Nobel Lecture). Angew. Chem. Int. Ed. 41, 2008–2022 (2002).
2. Sharpless, K. B. Searching for New Reactivity (Nobel Lecture). Angew. Chem. Int. Ed. 41, 2024–2032 (2002).
3. Knowles, W. S. Asymmetric Hydrogenations (Nobel Lecture 2001). Adv. Synth. Catal. 345, 3–13 (2003).
4. Nishikawa, Y. Recent topics in dual hydrogen bonding catalysis. Tetrahedron Lett. 59, 216–223 (2018).
5. Doyle, A. G. & Jacobsen, E. N. Small-Molecule H-Bond Donors in Asymmetric Catalysis. Chem. Rev. 107, 5713–5743 (2007).
6. Brak, K. & Jacobsen, E. N. Asymmetric Ion-Pairing Catalysis. Angew. Chem. Int. Ed. 52, 534–561 (2013).
7. García-Mancheño, O. Anion-Binding Catalysis. (John Wiley & Sons, 2022).
8. Knowles, R. R. & Jacobsen, E. N. Attractive noncovalent interactions in asymmetric catalysis: Links between enzymes and small molecule catalysts. Proc. Natl. Acad. Sci. 107, 20678–20685 (2010).
9. Nishibayashi, Y., Inada, Y., Hidai, M. & Uemura, S. Ruthenium-Catalyzed Carbon−Carbon Bond Formation between Propargylic Alcohols and Alkenes via the Allenylidene-Ene Reaction. J. Am. Chem. Soc. 125, 6060–6061 (2003).
10. Pfaltz, A. & Drury, W. J. Design of chiral ligands for asymmetric catalysis: From C2-symmetric P,P- and N,N-ligands to sterically and electronically nonsymmetrical P,N-ligands. Proc. Natl. Acad. Sci. 101, 5723–5726 (2004).
11. Ranieri, B., Escofet, I. & Echavarren, A. M. Anatomy of gold catalysts: facts and myths. Org. Biomol. Chem. 13, 7103–7118 (2015).
12. Michaelson, R. C., Palermo, R. E. & Sharpless, K. B. Chiral hydroxamic acids as ligands in the vanadium catalyzed asymmetric epoxidation of allylic alcohols by tert-butyl hydroperoxide. J. Am. Chem. Soc. 99, 1990–1992 (1977).
13. Yoshino, T., Satake, S. & Matsunaga, S. Diverse Approaches for Enantioselective C−H Functionalization Reactions Using Group 9 CpXMIII Catalysts. Chem. – Eur. J. 26, 7346–7357 (2020).
14. Phipps, R. J., Hamilton, G. L. & Toste, F. D. The progression of chiral anions from concepts to applications in asymmetric catalysis. Nat. Chem. 4, 603–614 (2012).
15. Mahlau, M. & List, B. Asymmetric Counteranion-Directed Catalysis: Concept, Definition, and Applications. Angew. Chem. Int. Ed. 52, 518–533 (2013).
16. Hamilton, G. L., Kang, E. J., Mba, M. & Toste, F. D. A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis. Science 317, 496–499 (2007).
17. Mukherjee, S. & List, B. Chiral Counteranions in Asymmetric Transition-Metal Catalysis: Highly Enantioselective Pd/Brønsted Acid-Catalyzed Direct α-Allylation of Aldehydes. J. Am. Chem. Soc. 129, 11336–11337 (2007).
18. Satake, S. et al. Pentamethylcyclopentadienyl rhodium(III)–chiral disulfonate hybrid catalysis for enantioselective C–H bond functionalization. Nat. Catal. 1, 585–591 (2018).
19. Raducan, M., Moreno, M., Bour, C. & Echavarren, A. M. Phosphate ligands in the gold(I)-catalysed activation of enynes. Chem. Commun. 48, 52–54 (2012).
20. Kündig, E. P., Saudan, C. M. & Bernardinelli, G. A Stable and Recoverable Chiral Ru Lewis Acid: Synthesis, Asymmetric Diels–Alder Catalysis and Structure of the Lewis Acid Methacrolein Complex. Angew. Chem. Int. Ed. 38, 1219–1223 (1999).
21. Alvarez, S. Coordinating Ability of Anions, Solvents, Amino Acids, and Gases towards Alkaline and Alkaline-Earth Elements, Transition Metals, and Lanthanides. Chem. – Eur. J. 26, 4350–4377 (2020).
22. Nguyen, B. N. et al. Deconvolution of the Mechanism of Homogeneous Gold-Catalyzed Reactions. Organometallics 31, 2395–2402 (2012).
23. Jindal, G. & Sunoj, R. B. Mechanistic Insights on Cooperative Asymmetric Multicatalysis Using Chiral Counterions. J. Org. Chem. 79, 7600–7606 (2014).
24. Biasiolo, L. et al. Unexpected Anion Effect in the Alkoxylation of Alkynes Catalyzed by N-Heterocyclic Carbene (NHC) Cationic Gold Complexes. Chem. – Eur. J. 20, 14594–14598 (2014).
25. Klausen, R. S. & Jacobsen, E. N. Weak Brønsted Acid−Thiourea Co-catalysis: Enantioselective, Catalytic Protio-Pictet−Spengler Reactions. Org. Lett. 11, 887–890 (2009).
26. Xu, H., Zuend, S. J., Woll, M. G., Tao, Y. & Jacobsen, E. N. Asymmetric Cooperative Catalysis of Strong Brønsted Acid–Promoted Reactions Using Chiral Ureas. Science 327, 986–990 (2010).
27. Banik, S. M., Levina, A., Hyde, A. M. & Jacobsen, E. N. Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis. Science 358, 761–764 (2017).
28. Trotta, A. H. & Jacobsen, E. N. in Anion-Binding Catalysis (ed García-Mancheño, O.) Ch. 4, 141–159 (John Wiley & Sons, Ltd, 2022).
29. Mo, J. & Xiao, J. The Heck Reaction of Electron-Rich Olefins with Regiocontrol by Hydrogen-Bond Donors. Angew. Chem. Int. Ed. 45, 4152–4157 (2006).
30. Ruan, J., Iggo, J. A., Berry, N. G. & Xiao, J. Hydrogen-Bonding-Promoted Oxidative Addition and Regioselective Arylation of Olefins with Aryl Chlorides. J. Am. Chem. Soc. 132, 16689–16699 (2010).
31. Farney, E. P. et al. Discovery and Elucidation of Counteranion Dependence in Photoredox Catalysis. J. Am. Chem. Soc. 141, 6385–6391 (2019).
32. Franchino, A., Martí, À., Nejrotti, S. & Echavarren, A. M. Silver-Free Au(I) Catalysis Enabled by Bifunctional Urea- and Squaramide-Phosphine Ligands via H-Bonding. Chem. – Eur. J. 27, 11989–11996 (2021).
33. Franchino, A., Martí, À. & Echavarren, A. M. H-Bonded Counterion-Directed Enantioselective Au(I) Catalysis. J. Am. Chem. Soc. 144, 3497–3509 (2022).
34. Zhang, X. et al. Asymmetric Azide–Alkyne Cycloaddition with Ir(I)/Squaramide Cooperative Catalysis: Atroposelective Synthesis of Axially Chiral Aryltriazoles. J. Am. Chem. Soc. 144, 6200–6207 (2022).
35. Hu, Q., He, Z., Peng, L. & Guo, C. Combining nickel and squaramide catalysis for the stereodivergent α-propargylation of oxindoles. Nat. Synth. 1, 322–331 (2022).
36. Li, M.-L., Yu, J.-H., Li, Y.-H., Zhu, S.-F. & Zhou, Q.-L. Highly enantioselective carbene insertion into N–H bonds of aliphatic amines. Science 366, 990–994 (2019).
37. Furniel, L. G., Echemendía, R. & Burtoloso, A. C. B. Cooperative copper-squaramide catalysis for the enantioselective N–H insertion reaction with sulfoxonium ylides. Chem. Sci. 12, 7453–7459 (2021).
38. Simlandy, A. K., Ghosh, B. & Mukherjee, S. Enantioselective [4 + 2]-Annulation of Azlactones with Copper-Allenylidenes under Cooperative Catalysis: Synthesis of α-Quaternary α-Acylaminoamides. Org. Lett. 21, 3361–3366 (2019).
39. Guan, Y., Attard, J. W., Visco, M. D., Fisher, T. J. & Mattson, A. E. Enantioselective Catalyst Systems from Copper(II) Triflate and BINOL–Silanediol. Chem. – Eur. J. 24, 7123–7127 (2018).
40. Nishibayashi, Y., Wakiji, I. & Hidai, M. Novel Propargylic Substitution Reactions Catalyzed by Thiolate-Bridged Diruthenium Complexes via Allenylidene Intermediates. J. Am. Chem. Soc. 122, 11019–11020 (2000).
41. Miyake, Y., Uemura, S. & Nishibayashi, Y. Catalytic Propargylic Substitution Reactions. ChemCatChem 1, 342–356 (2009).
42. Nishibayashi, Y. et al. Ruthenium-Catalyzed Propargylic Substitution Reactions of Propargylic Alcohols with Oxygen-, Nitrogen-, and Phosphorus-Centered Nucleophiles. Chem. – Eur. J. 11, 1433–1451 (2005).
43. Nishibayashi, Y., Yoshikawa, M., Inada, Y., Hidai, M. & Uemura, S. Ruthenium-Catalyzed Propargylation of Aromatic Compounds with Propargylic Alcohols. J. Am. Chem. Soc. 124, 11846–11847 (2002).
44. Fukamizu, K., Miyake, Y. & Nishibayashi, Y. Ruthenium-Catalyzed Enantioselective Carbon−Carbon Bond Forming Reaction via Allenylidene-Ene Process: Synthetic Approach to Chiral Heterocycles Such As Chromane, Thiochromane, and 1,2,3,4-Tetrahydroquinoline Derivatives. J. Am. Chem. Soc. 130, 10498–10499 (2008).
45. Reisman, S. E., Doyle, A. G. & Jacobsen, E. N. Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions. J. Am. Chem. Soc. 130, 7198–7199 (2008).
46. Lehnherr, D., Ford, D. D., Bendelsmith, A. J., Kennedy, C. R. & Jacobsen, E. N. Conformational Control of Chiral Amido-Thiourea Catalysts Enables Improved Activity and Enantioselectivity. Org. Lett. 18, 3214–3217 (2016).
47. Kennedy, C. R. et al. Mechanism-Guided Development of a Highly Active Bis-thiourea Catalyst for Anion-Abstraction Catalysis. J. Am. Chem. Soc. 138, 13525–13528 (2016).
48. Park, Y. et al. Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions. Science 355, 162–166 (2017).
49. Levi, S. M., Li, Q., Rötheli, A. R. & Jacobsen, E. N. Catalytic activation of glycosyl phosphates for stereoselective coupling reactions. Proc. Natl. Acad. Sci. 116, 35–39 (2019).
50. Mayfield, A. B., Metternich, J. B., Trotta, A. H. & Jacobsen, E. N. Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors. J. Am. Chem. Soc. 142, 4061–4069 (2020).
51. Li, Q., Levi, S. M., Wagen, C. C., Wendlandt, A. E. & Jacobsen, E. N. Site-selective, stereocontrolled glycosylation of minimally protected sugars. Nature 608, 74–79 (2022).
52. Knowles, R. R., Lin, S. & Jacobsen, E. N. Enantioselective Thiourea-Catalyzed Cationic Polycyclizations. J. Am. Chem. Soc. 132, 5030–5032 (2010).
53. Ronchi, E., Paradine, S. M. & Jacobsen, E. N. Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions. J. Am. Chem. Soc. 143, 7272–7278 (2021).
54. Taylor, M. S., Tokunaga, N. & Jacobsen, E. N. Enantioselective Thiourea-Catalyzed Acyl-Mannich Reactions of Isoquinolines. Angew. Chem. Int. Ed. 44, 6700–6704 (2005).
55. Raheem, I. T., Thiara, P. S., Peterson, E. A. & Jacobsen, E. N. Enantioselective Pictet−Spengler-Type Cyclizations of Hydroxylactams: H-Bond Donor Catalysis by Anion Binding. J. Am. Chem. Soc. 129, 13404–13405 (2007).
56. Liao, S. & List, B. Asymmetric Counteranion-Directed Transition-Metal Catalysis: Enantioselective Epoxidation of Alkenes with Manganese(III) Salen Phosphate Complexes. Angew. Chem. Int. Ed. 49, 628–631 (2010).
57. Myers, B. J. Common Solvents Used in Organic Chemistry: Table of Properties. https://organicchemistrydata.org/solvents/ (2005).