Controlling
Quasdorf, K. W. & Overman, L. E. Catalytic enantioselective synthesis of quaternary carbon stereocentres. Nature 516, 181–191 (2014).
Google Scholar
Zeng, X.-P., Cao, Z.-Y., Wang, Y.-H., Zhou, F. & Zhou, J. Catalytic enantioselective desymmetrization reactions to all-carbon quaternary stereocenters. Chem. Rev. 116, 7330–7396 (2016).
Google Scholar
Feng, J., Holmes, M. & Krische, M. J. Acyclic quaternary carbon stereocenters via enantioselective transition metal catalysis. Chem. Rev. 117, 12564–12580 (2017).
Google Scholar
Wu, Y. & Wang, P. Silicon-stereogenic monohydrosilane: synthesis and applications. Angew. Chem. Int. Ed. 61, e202205382 (2022).
Google Scholar
Xu, L.-W., Li, L., Lai, G.-Q. & Jiang, J.-X. The recent synthesis and application of silicon-stereogenic silanes: a renewed and significant challenge in asymmetric synthesis. Chem. Soc. Rev. 40, 1777–1790 (2011).
Google Scholar
Grabulosa, A., Granell, J. & Muller, G. Preparation of optically pure P-stereogenic trivalent phosphorus compounds. Coord. Chem. Rev. 251, 25–90 (2007).
Google Scholar
Dutartre, M., Bayardon, J. & Jugé, S. Applications and stereoselective syntheses of P-chirogenic phosphorus compounds. Chem. Soc. Rev. 45, 5771–5794 (2016).
Google Scholar
Fernández, I. & Khiar, N. Recent developments in the synthesis and utilization of chiral sulfoxides. Chem. Rev. 103, 3651–3706 (2003).
Google Scholar
Han, J., Soloshonok, V. A., Klika, K. D., Drabowicz, J. & Wzorek, A. Chiral sulfoxides: advances in asymmetric synthesis and problems with the accurate determination of the stereochemical outcome. Chem. Soc. Rev. 47, 1307–1350 (2018).
Google Scholar
Walsh, M. P., Phelps, J. M., Lennon, M. E., Yufit, D. S. & Kitching, M. O. Enantioselective synthesis of ammonium cations. Nature 597, 70–76 (2021).
Google Scholar
Luo, Z. et al. Ionic hydrogen bond-assisted catalytic construction of nitrogen stereogenic center via formal desymmetrization of remote diols. Angew. Chem. Int. Ed. 63, e202404979 (2024).
Google Scholar
Bhadra, S. & Yamamoto, H. Catalytic asymmetric synthesis of N-chiral amine oxides. Angew. Chem. Int. Ed. 55, 13043–13046 (2016).
Google Scholar
Chattopadhyay, A. K. & Hanessian, S. Recent progress in the chemistry of daphniphyllum alkaloids. Chem. Rev. 117, 4104–4146 (2017).
Google Scholar
Yuan, R. et al. The first direct synthesis of chiral Tröger’s bases catalyzed by chiral glucose-containing pyridinium ionic liquids. Chem. Eng. J. 316, 1026–1034 (2017).
Google Scholar
Huang, S. et al. Organocatalytic enantioselective construction of chiral azepine skeleton bearing multiple-stereogenic elements. Angew. Chem. Int. Ed. 60, 21486–21493 (2021).
Google Scholar
Ma, C., Sun, Y., Yang, J., Guo, H. & Zhang, J. Catalytic asymmetric synthesis of Tröger’s base analogues with nitrogen stereocenter. ACS Cent. Sci. 9, 64–71 (2023).
Google Scholar
Yu, T. et al. Immobilizing stereogenic nitrogen center in doubly fused triarylamines through palladium-catalyzed asymmetric C−H activation/seven-membered-ring formation. ACS Catal. 13, 9688–9694 (2023).
Google Scholar
Annunziata, R., Fornasier, R. & Montanari, F. Compounds with molecular asymmetry due solely to a tercovalent non-bridgehead nitrogen atom: optically active N-chloro-2,2-diphenylaziridine. J. Chem. Soc. Chem. Commun. 1972, 1133–1134 (1972).
Google Scholar
Forni, A., Moretti, I., Prosyanik, A. V. & Torre, G. Optically active trifluoromethylcarbinols as chiral solvating agents for asymmetric transformations at a ring-nitrogen atom. J. Chem. Soc. Chem. Commun. 1981, 588–590 (1981).
Google Scholar
Bucciarelli, M., Forni, A., Moretti, I. & Torre, G. Optically active trifluoromethylcarbinols as chiral solvating agents for asymmetric transformations at a ring-nitrogen atom. Synthesis of optically active N-chloroaziridines and stereochemical aspects of chiral solvent-aziridine solute complexes. J. Org. Chem. 48, 2640–2644 (1983).
Google Scholar
Shustov, G. V. et al. Asymmetric nitrogen. 72. Geminal systems. 46. N-chlorooxaziridines: optical activation, absolute configuration, and chiroptical properties. J. Am. Chem. Soc. 111, 4210–4215 (1989).
Google Scholar
Montanari, F., Moretti, I. & Torre, G. Asymmetric introduction at trivalent nitrogen. Optically active 2-methyl-3,3-diphenyloxaziridine, a compound with molecular asymmetry due solely to the nitrogen atom. Chem. Commun. 1968, 1694–1695 (1968).
Boyd, D. R. Optically active oxaziridines. Tetrahedron Lett. 9, 4561–4564 (1968).
Google Scholar
Kostyanovsky, R. G., Rudchenko, V. F., Shtamburg, V. G., Chervin, I. I. & Nasibov, S. S. Asymmetrical nonbridgehead nitrogen—XXVI. Synthesis, configurational stability, and resolution of N,N-dialkoxyamines into antipodes. Tetrahedron 37, 4245–4254 (1981).
Google Scholar
Smith, O. et al. Control of stereogenic oxygen in a helically chiral oxonium ion. Nature 615, 430–435 (2023).
Google Scholar
Porto, C. M., de Barros, G. A., Santana, L. C., Moralles, A. C. & Morgon, N. H. Ammonia quantum tunneling in cold rare-gas He and Ar clusters and factorial design approach for methodology evaluation. J. Mol. Model. 28, 293 (2022).
Google Scholar
Adams, R. & Cairns, T. L. Attempts to prepare optically active ethyleneimine derivatives containing an asymmetric nitrogen atom. J. Am. Chem. Soc. 61, 2464–2467 (1939).
Google Scholar
Dunlop, H. G. & Tucker, S. H. Attempts to prepare optically active tervalent nitrogen compounds. Part I. Syntheses of 1:9-phenylenecarbazole and derivatives. J. Chem. Soc. 1939, 1945–1956 (1939).
Google Scholar
Brois, S. J. Aziridines. XII. Isolation of a stable nitrogen pyramid. J. Am. Chem. Soc. 90, 508–509 (1968).
Google Scholar
Rauk, A., Allen, L. C. & Mislow, K. Pyramidal inversion. Angew. Chem. Int. Ed. 9, 400–414 (1970).
Google Scholar
Zaitseva, S. & Köhler, V. Pyramidal stereogenic nitrogen centers (SNCs). Synthesis 57, 1237–1254 (2025).
Google Scholar
Shtamburg, V. G. et al. Reactions of N-chloro-N-alkoxy-tert-alkylamines with isobutylene and methanol. Russ. Chem. Bull. 40, 951–954 (1991).
Google Scholar
Rudchenko, V. F. & Kostyanovskii, R. G. Geminal oxygen–nitrogen–halogen systems. N-halohydroxylamine derivatives. Russ. Chem. Rev. 67, 179–192 (1998).
Google Scholar
Wendlandt, A. E., Vangal, P. & Jacobsen, E. N. Quaternary stereocentres via an enantioconvergent catalytic SN1 reaction. Nature 556, 447–451 (2018).
Google Scholar
Singh, V. K. et al. Taming secondary benzylic cations in catalytic asymmetric SN1 reactions. Science 382, 325–329 (2023).
Google Scholar
Zhang, X. et al. An enantioconvergent halogenophilic nucleophilic substitution (SN2X) reaction. Science 363, 400–404 (2019).
Google Scholar
Lovinger, G. J., Sak, M. H. & Jacobsen, E. N. Catalysis of an SN2 pathway by geometric preorganization. Nature 632, 1052–1059 (2024).
Google Scholar
Denmark, S. E., Kuester, W. E. & Burk, M. T. Catalytic, asymmetric halofunctionalization of alkenes—a critical perspective. Angew. Chem. Int. Ed. 51, 10938–10953 (2012).
Google Scholar
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).
Google Scholar
Uraguchi, D. & Terada, M. Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation. J. Am. Chem. Soc. 126, 5356–5357 (2004).
Google Scholar
Akiyama, T. Stronger Brønsted acids. Chem. Rev. 107, 5744–5758 (2007).
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; Brønsted acidity, hydrogen bonding, ion pairing and metal phosphates. Chem. Rev. 114, 9047–9153 (2014).
Google Scholar
Reisman, S. E., Doyle, A. G. & Jacobsen, E. N. Enantioselective thiourea-catalyzed additions to oxocarbenium ions. J. Am. Chem. Soc. 130, 7198–7199 (2008).
Google Scholar
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).
Google Scholar
Zhou, H. et al. Organocatalytic stereoselective cyanosilylation of small ketones. Nature 605, 84–89 (2022).
Google Scholar
Wang, M. et al. Asymmetric hydrogenation of ketimines with minimally different alkyl groups. Nature 631, 556–562 (2024).
Google Scholar
Frisch, M. J. et al. Gaussian 16, Revision A.03 (Gaussian, 2016).
Becke, A. D. Density‐functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648–5652 (1993).
Google Scholar
Lee, C., Yang, W. & Parr, R. G. Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785–789 (1988).
Google Scholar
Grimme, S., Antony, J., Ehrlich, S. & Krieg, H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H–Pu. J. Chem. Phys. 132, 154104 (2010).
Google Scholar
Grimme, S., Ehrlich, S. & Goerigk, L. Effect of the damping function in dispersion corrected density functional theory. J. Comput. Chem. 32, 1456–1465 (2011).
Google Scholar
Chai, J.-D. & Head-Gordon, M. Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Phys. Chem. Chem. Phys. 10, 6615–6620 (2008).
Google Scholar
Marenich, A. V., Cramer, C. J. & Truhlar, D. G. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J. Phys. Chem. B 113, 6378–6396 (2009).
Google Scholar
Bickelhaupt, F. M. & Houk, K. N. Analyzing reaction rates with the distortion/interaction‐activation strain model. Angew. Chem. Int. Ed. 56, 10070–10086 (2017).
Google Scholar
Duan, M. et al. Chiral phosphoric acid catalyzed conversion of epoxides into thiiranes: mechanism, stereochemical model, and new catalyst design. Angew. Chem. Int. Ed. 61, e202113204 (2022).
Google Scholar
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