Mulliken, R. S. Structures of complexes formed by halogen molecules with aromatic and with oxygenated solvents. J. Am. Chem. Soc. 72, 600–608 (1950).
Mulliken, R. S. Molecular compounds and their spectra. III. The interaction of electron donors and acceptors. J. Phys. Chem. 56, 801–822 (1952).
Mulliken, R. S. Molecular compounds and their spectra. II. J. Am. Chem. Soc. 74, 811–824 (1952).
Lima, C. G. S. et al. Organic synthesis enabled by light-irradiation of EDA complexes: theoretical background and synthetic applications. ACS Catal. 6, 1389–1407 (2016).
Mondal, S. et al. Enantioselective radical reactions using chiral catalysts. Chem. Rev. 122, 5842–5976 (2022).
Article PubMed CAS Google Scholar
Wang, P.-Z., Xiao, W.-J. & Chen, J.-R. Light-empowered contra-thermodynamic stereochemical editing. Nat. Rev. Chem. 7, 35–50 (2023).
Wortman, A. K. & Stephenson, C. R. J. EDA photochemistry: mechanistic investigations and future opportunities. Chem 9, 2390–2415 (2023).
Article PubMed PubMed Central CAS Google Scholar
Prier, C. K., Rankic, D. A. & MacMillan, D. W. C. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem. Rev. 113, 5322–5322 (2013).
Article PubMed PubMed Central CAS Google Scholar
Shaw, M. H., Twilton, J. & MacMillan, D. W. C. Photoredox catalysis in organic chemistry. J. Org. Chem. 81, 6898–6926 (2016).
Article PubMed PubMed Central CAS Google Scholar
Arceo, E., Jurberg, I. D., Álvarez-Fernández, A. & Melchiorre, P. Photochemical activity of a key donor–acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes. Nat. Chem. 5, 750–756 (2013).
Article PubMed CAS Google Scholar
Arceo, E., Bahamonde, A., Bergonzini, G. & Melchiorre, P. Enantioselective direct α-alkylation of cyclic ketones by means of photo-organocatalysis. Chem. Sci. 5, 2438–2442 (2014).
Bahamonde, A. & Melchiorre, P. Mechanism of the stereoselective α-alkylation of aldehydes driven by the photochemical activity of enamines. J. Am. Chem. Soc. 138, 8019–8030 (2016).
Article PubMed PubMed Central CAS Google Scholar
Cao, Z.-Y., Ghosh, T. & Melchiorre, P. Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex. Nat. Commun. 9, 3274 (2018).
Article PubMed PubMed Central Google Scholar
Woźniak, Ł, Murphy, J. J. & Melchiorre, P. Photo-organocatalytic enantioselective perfluoroalkylation of β-ketoesters. J. Am. Chem. Soc. 137, 5678–5681 (2015).
Article PubMed PubMed Central Google Scholar
Bauer, A., Westkämper, F., Grimme, S. & Bach, T. Catalytic enantioselective reactions driven by photoinduced electron transfer. Nature 436, 1139–1140 (2005).
Article PubMed CAS Google Scholar
Nicewicz, D. A. & MacMillan, D. W. C. Merging photoredox catalysis with organocatalysis: the direct asymmetric alkylation of aldehydes. Science 322, 77–80 (2008).
Article PubMed PubMed Central CAS Google Scholar
Huo, H. et al. Asymmetric photoredox transition-metal catalysis activated by visible light. Nature 515, 100–103 (2014).
Article PubMed CAS Google Scholar
Blum, T. R. et al. Enantioselective photochemistry through Lewis acid-catalyzed triplet energy transfer. Science 354, 1391–1395 (2016).
Article PubMed PubMed Central CAS Google Scholar
Yao, W., Bazan-Bergamino, E. A. & Ngai, M.-Y. Asymmetric photocatalysis enabled by chiral organocatalysts. ChemCatChem 14, e202101292 (2022).
Article PubMed CAS Google Scholar
Hölzl-Hobmeier, A. et al. Catalytic deracemization of chiral allenes by sensitized excitation with visible light. Nature 564, 240–243 (2018).
Akiyama, T., Itoh, J., Yokota, K. & Fuchibe, K. Enantioselective Mannich-type reaction catalyzed by a chiral Brønsted acid. Angew. Chem. Int. Ed. 43, 1566–1568 (2004).
Uraguchi, D. & Terada, M. Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. J. Am. Chem. Soc. 126, 5356–5357 (2004).
Article PubMed CAS Google Scholar
Parmar, D., Sugiono, E., Raja, S. & Rueping, M. Complete field guide to asymmetric BINOL-phosphate derived Brønsted acid and metal catalysis: history and classification by mode of activation; Bønsted acidity, hydrogen bonding, ion pairing, and metal phosphates. Chem. Rev. 114, 9047–9153 (2014).
Article PubMed CAS Google Scholar
Cussac, M., Boucherle, A., Pierre, J. L. & Hache, J. Pyridyl ketones of biological interest (chalcone analogs). VI. Alcohol derivatives of azachalcones with depressant activity on the central nervous system. Eur. J. Med. Chem. 9, 651–657 (1974).
Lin, T. K. et al. Quantum statistical calculation for the correlation of biological activity and chemical structure. 3. Disopyramide phosphate and related compounds as antiarrhythmic agents. J. Med. Chem. 17, 751–753 (1974).
Article PubMed CAS Google Scholar
Yen, C. H., Lowrie, H. S. & Dean, R. R. Compounds related to 4-diisopropylamino-2-phenyl-2-(2-pyridyl)butyramide. Synthesis and antiarrhythmic activity. J. Med. Chem. 17, 1131–1135 (1974).
Article PubMed CAS Google Scholar
Rennison, D. et al. Synthesis and activity studies of analogues of the rat selective toxicant norbormide. Bioorg. Med. Chem. 15, 2963–2974 (2007).
Article PubMed CAS Google Scholar
Rehdorf, J. et al. Pseudomonas putida esterase contains A GGG(A)X-motif confering activity for the kinetic resolution of tertiary alcohols. Appl. Microbio. Biotech. 93, 1119–1126 (2012).
Harikrishnan, L. S. et al. Diphenylpyridylethanamine (DPPE) derivatives as cholesteryl ester transfer protein (CETP) inhibitors. J. Med. Chem. 55, 6162–6175 (2012).
Article PubMed CAS Google Scholar
Huang, A. et al. Discovery of 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid (PSI-421), a P-Selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury. J. Med. Chem. 53, 6003–6017 (2010).
Hou, L. et al. Enantioselective radical addition to ketones through Lewis acid-enabled photoredox catalysis. J. Am. Chem. Soc. 144, 22140–22149 (2022).
Article PubMed CAS Google Scholar
Yin, Y., Zhao, X. & Jiang, Z. Asymmetric photocatalytic synthesis of enantioenriched azaarene derivatives. Chin. J. Org. Chem. 42, 1609–1625 (2022).
Yin, Y. et al. Conjugate addition–enantioselective protonation of N-aryl glycines to α-branched 2-vinylazaarenes via cooperative photoredox and asymmetric catalysis. J. Am. Chem. Soc. 140, 6083–6087 (2018).
Article PubMed CAS Google Scholar
Liu, Y. et al. Asymmetric olefin isomerization via photoredox catalytic hydrogen atom transfer and enantioselective protonation. J. Am. Chem. Soc. 145, 18307–18315 (2023).
Comments (0)