Noyori, R. Synthesizing our future. Nat. Chem. 1, 5–6 (2009).

Article  CAS  PubMed  Google Scholar 

Shenvi, R. A., O’Malley, D. P. & Baran, P. S. Chemoselectivity: the mother of invention in total synthesis. Acc. Chem. Res. 42, 530–541 (2009).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Afagh, N. A. & Yudin, A. K. Chemoselectivity and the curious reactivity preferences of functional groups. Angew. Chem. Int. Ed. 49, 262–310 (2010).

Article  CAS  Google Scholar 

Huang, Z. & Dong, G. Site-selectivity control in organic reactions: a quest to differentiate reactivity among the same kind of functional groups. Acc. Chem. Res. 50, 465–471 (2017).

Article  CAS  PubMed  Google Scholar 

Govaerts, S., Angelini, L., Hampton, C., Malet-Sanz, L., Ruffoni, A. & Leonori, D. Photoinduced olefin diamination with alkylamines. Angew. Chem. Int. Ed. 59, 15021–15028 (2020).

Article  CAS  Google Scholar 

Holst, D. E., Dorval, C., Winter, C. K., Guzei, I. A. & Wickens, Z. K. Regiospecific alkene aminofunctionalization via an electrogenerated dielectrophile. J. Am. Chem. Soc. 145, 8299–8307 (2023).

Article  CAS  Google Scholar 

Bar, G. L. J., Lloyd-Jones, G. C. & Booker-Milburn, K. I. Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes. J. Am. Chem. Soc. 127, 7308–7309 (2005).

Article  CAS  PubMed  Google Scholar 

Zhu, Y., Cornwall, R. G., Du, H., Zhao, B. & Shi, Y. Catalytic diamination of olefins via N–N bond activation. Acc. Chem. Res. 47, 3665–3678 (2014).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Liu, Y., Xie, Y., Wang, H. & Huang, H. Enantioselective aminomethylamination of conjugated dienes with aminals enabled by chiral palladium complex-catalyzed C–N bond activation. J. Am. Chem. Soc. 138, 4314–4317 (2016).

Article  CAS  PubMed  Google Scholar 

Fu, N., Sauer, G. S., Saha, A., Loo, A. & Lin, S. Metal-catalyzed electrochemical diazidation of alkenes. Science 357, 575–579 (2017).

Article  CAS  PubMed  Google Scholar 

Muñiz, K., Barreiro, L., Romero, R. M. & Martínez, C. Catalytic asymmetric diamination of styrenes. J. Am. Chem. Soc. 139, 4354–4357 (2017).

Article  PubMed  Google Scholar 

Chen, C., Luo, Y., Fu, L., Chen, P., Lan, Y. & Liu, G. Palladium-catalyzed intermolecular ditrifluoromethoxylation of unactivated alkenes: CF3O-palladation initiated by Pd(IV). J. Am. Chem. Soc. 140, 1207–1210 (2018).

Article  CAS  PubMed  Google Scholar 

Tao, Z., Gilbert, B. B. & Denmark, S. E. Catalytic, enantioselective syn-diamination of alkenes. J. Am. Chem. Soc. 141, 19161–19170 (2019).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Minakata, S., Miwa, H., Yamamoto, K., Hirayama, A. & Okumura, S. Diastereodivergent intermolecular 1,2-diamination of unactivated alkenes enabled by iodine catalysis. J. Am. Chem. Soc. 143, 4112–4118 (2021).

Article  CAS  PubMed  Google Scholar 

Tian, B., Chen, P., Leng, X. & Liu, G. Palladium-catalysed enantioselective diacetoxylation of terminal alkenes. Nat. Catal. 4, 172–179 (2021).

Article  CAS  Google Scholar 

Buller, R., Lutz, S., Kazlauskas, R. J., Snajdrova, R., Moore, J. C. & Bornscheuer, U. T. From nature to industry: harnessing enzymes for biocatalysis. Science 382, eadh8615 (2023).

Article  CAS  PubMed  Google Scholar 

Almhjell, P. J., Boville, C. E. & Arnold, F. H. Engineering enzymes for noncanonical amino acid synthesis. Chem. Soc. Rev. 47, 8980–8997 (2018).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Viso, A., Fernandez, R., Garcia, A. & Flores, A. α, β-Diamino acids: biological significance and synthetic approaches. Chem. Rev. 105, 3167–3196 (2005).

Article  CAS  PubMed  Google Scholar 

Kittakoop, P., Mahidol, C. & Ruchirawat, S. Alkaloids as important scaffolds in therapeutic drugs for the treatments of cancer, tuberculosis, and smoking cessation. Curr. Top. Med. Chem. 14, 239–252 (2013).

Article  Google Scholar 

Vitaku, E., Smith, D. T. & Njardarson, J. T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J. Med. Chem. 57, 10257–10274 (2014).

Article  CAS  PubMed  Google Scholar 

Tan, G., Das, M., Kleinmans, R., Katzenburg, F., Daniliuc, C. & Glorius, F. Energy transfer-enabled unsymmetrical diamination using bifunctional nitrogen-radical precursors. Nat. Catal. 5, 1120–1130 (2022).

Article  CAS  Google Scholar 

Lawrence, S. A. Amines: Synthesis, Properties and Applications Vol. 1 (Cambridge Univ. Press, 2004).

Ali, S. Z., Budaitis, B. G., Fontaine, D. F. A., Pace, A. L., Garwin, J. A. & White, M. C. Allylic C–H amination cross-coupling furnishes tertiary amines by electrophilic metal catalysis. Science 376, 276–283 (2022).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Jin, Y., Jing, Y., Li, C., Li, M., Wu, W., Ke, Z. & Jiang, H. Palladium-catalysed selective oxidative amination of olefins with Lewis basic amines. Nat. Chem. 14, 1118–1125 (2022).

Article  CAS  PubMed  Google Scholar 

Ramström, O. & Lehn, J. M. Drug discovery by dynamic combinatorial libraries. Nat. Rev. Drug Discov. 1, 26–36 (2002).

Article  PubMed  Google Scholar 

Jin, Y., Yu, C., Denman, R. J. & Zhang, W. Recent advances in dynamic covalent chemistry. Chem. Soc. Rev. 42, 6634–6654 (2013).

Article  CAS  PubMed  Google Scholar 

Mondal, M. & Hirsch, A. K. H. Dynamic combinatorial chemistry: a tool to facilitate the identification of inhibitors for protein targets. Chem. Soc. Rev. 44, 2455–2488 (2015).

Article  CAS  PubMed  Google Scholar 

de Figueiredo, R. M. Transition-metal-catalyzed diamination of olefins. Angew. Chem. Int. Ed. 48, 1190–1193 (2009).

Article  Google Scholar 

Cardona, F. & Goti, A. Metal-catalysed 1,2-diamination reactions. Nat. Chem. 1, 269–275 (2009).

Article  CAS  PubMed  Google Scholar 

Zhang, H., Jiang, T., Zhang, J. & Huang, H. Catalytic reactions directed by a structurally well-defined aminomethyl cyclopalladated complex. Acc. Chem. Res. 54, 4305–4318 (2021).

Article  CAS  PubMed  Google Scholar 

Kanzian, T., Nigst, T. A., Maier, A., Pichl, S. & Mayr, H. Nucleophilic reactivities of primary and secondary amines in acetonitrile. Eur. J. Org. Chem. 2009, 6379–6385 (2009).

Article  Google Scholar 

Xiong, Y., Sun, Y. & Zhang, G. Recent advances on catalytic asymmetric difunctionalization of 1,3-dienes. Tetrahedron Lett 59, 347–355 (2018).

Article  CAS  Google Scholar 

Li, G., Huo, X., Jiang, X. & Zhang, W. Asymmetric synthesis of allylic compounds via hydrofunctionalisation and difunctionalisation of dienes, allenes, and alkynes. Chem. Soc. Rev. 49, 2060–2118 (2020).

Article  CAS  PubMed  Google Scholar 

Yu, B., Zou, S., Liu, H. & Huang, H. Palladium-catalyzed ring-closing reaction via C–N bond metathesis for rapid construction of saturated N-heterocycles. J. Am. Chem. Soc. 142, 18341–18345 (2020).

Article  CAS  PubMed