Nugent, T. C. (ed.) Chiral Amine Synthesis: Methods, Developments and Applications (Wiley-VCH, 2010).

Li, W. & Zhang, X. (eds) Stereoselective Formation of Amines (Springer, 2014).

Blaskovich, M. A. T. Unusual amino acids in medicinal chemistry. J. Med. Chem. 59, 10807–10836 (2016).

Article  CAS  PubMed  Google Scholar 

Vogt, H. & Bräse, S. Recent approaches towards the asymmetric synthesis of α,α-disubstituted α-amino acids. Org. Biomol. Chem. 5, 406–430 (2007).

Article  CAS  PubMed  Google Scholar 

Metz, A. E. & Kozlowski, M. C. Recent advances in asymmetric catalytic methods for the formation of acyclic α,α-disubstituted α-amino acids. J. Org. Chem. 80, 1–7 (2015).

Article  CAS  PubMed  Google Scholar 

Nájera, C. & Sansano, J. M. Catalytic asymmetric synthesis of α-amino acids. Chem. Rev. 107, 4584–4671 (2007).

Article  PubMed  Google Scholar 

Xie, J.-H., Zhu, S.-F. & Zhou, Q.-L. Transition metal-catalyzed enantioselective hydrogenation of enamines and imines. Chem. Rev. 111, 1713–1760 (2011).

Article  CAS  PubMed  Google Scholar 

Wang, H., Wen, J. & Zhang, X. Chiral tridentate ligands in transition metal-catalyzed asymmetric hydrogenation. Chem. Rev. 121, 7530–7567 (2021).

Article  CAS  PubMed  Google Scholar 

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).

Article  CAS  PubMed  Google Scholar 

Yang, Z.-P., Freas, D. J. & Fu, G. C. Asymmetric synthesis of protected unnatural α-amino acids via enantioconvergent nickel-catalyzed cross-coupling. J. Am. Chem. Soc. 143, 8614–8618 (2021).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Leonard, D. J., Ward, J. W. & Clayden, J. Asymmetric α-arylation of amino acids. Nature 562, 105–109 (2018).

Article  CAS  PubMed  Google Scholar 

Branca, M. et al. Memory of chirality of tertiary aromatic amides: a simple and efficient method for the enantioselective synthesis of quaternary α-amino acids. J. Am. Chem. Soc. 131, 10711–10718 (2009).

Article  CAS  PubMed  Google Scholar 

Kainz, Q. M. et al. Asymmetric copper-catalyzed C-N cross-couplings induced by visible light. Science 351, 681–684 (2016).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Li, Y. et al. Copper(II)-catalyzed asymmetric photoredox reactions: enantioselective alkylation of imines driven by visible light. J. Am. Chem. Soc. 140, 15850–15858 (2018).

Article  CAS  PubMed  Google Scholar 

Huo, X., Zhang, J., Fu, J., He, R. & Zhang, W. Ir/Cu dual catalysis: enantio- and diastereodivergent access to α,α-disubstituted α-amino acids bearing vicinal stereocenters. J. Am. Chem. Soc. 140, 2080–2084 (2018).

Article  CAS  PubMed  Google Scholar 

Wei, L. et al. Stereodivergent synthesis of α,α-disubstituted α-amino acids via synergistic Cu/Ir catalysis. J. Am. Chem. Soc. 140, 1508–1513 (2018).

Article  CAS  PubMed  Google Scholar 

Chen, W. & Hartwig, J. F. Control of diastereoselectivity for iridium-catalyzed allylation of a prochiral nucleophile with a phosphate counterion. J. Am. Chem. Soc. 135, 2068–2071 (2013).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Eftekhari-Sis, B. & Zirak, M. α-Imino esters in organic synthesis: recent advances. Chem. Rev. 117, 8326–8419 (2017).

Article  CAS  PubMed  Google Scholar 

Quan, M., Wu, L., Yang, G. & Zhang, W. Pd(ii), Ni(ii) and Co(ii)-catalyzed enantioselective additions of organoboron reagents to ketimines. Chem. Commun. 54, 10394–10404 (2018).

Article  CAS  Google Scholar 

Robak, M. T., Herbage, M. A. & Ellman, J. A. Synthesis and applications of tert-butanesulfinamide. Chem. Rev. 110, 3600–3740 (2010).

Article  CAS  PubMed  Google Scholar 

Ge, L. & Harutyunyan, S. R. in Catalytic Asymmetric Synthesis (eds Akiyama, T. & Ojima, I.) 619–659 (Wiley, 2022).

Denmark, S. E., Nakajima, N. & Nicaise, O. J.-C. Asymmetric addition of organolithium reagents to imines. J. Am. Chem. Soc. 116, 8797–8798 (1994).

Article  CAS  Google Scholar 

Fu, P., Snapper, M. L. & Hoveyda, A. H. Catalytic asymmetric alkylations of ketoimines. Enantioselective synthesis of N-substituted quaternary carbon stereogenic centers by Zr-catalyzed additions of dialkylzinc reagents to aryl-, alkyl-, and trifluoroalkyl-substituted ketoimines. J. Am. Chem. Soc. 130, 5530–5541 (2008).

Article  CAS  PubMed  Google Scholar 

Ortiz, P. et al. Copper-catalyzed enantioselective alkylation of enolizable ketimines with organomagnesium reagents. Angew. Chem. Int. Ed. 56, 3041–3044 (2017).

Article  CAS  Google Scholar 

Curto, J. M., Dickstein, J. S., Berritt, S. & Kozlowski, M. C. Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters. Org. Lett. 16, 1948–1951 (2014).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Blomberg, C. The Barbier Reaction and Related One-Step Processes (Springer, 1993).

Shen, A., Liu, M., Jia, Z.-S., Xu, M.-H. & Lin, G.-Q. One-pot synthesis of chiral α-methylene-γ-lactams with excellent diastereoselectivities and enantioselectivities. Org. Lett. 12, 5154–5157 (2010).

Article  CAS  PubMed  Google Scholar 

Friestad, G. K. & Qin, J. Highly stereoselective intermolecular radical addition to aldehyde hydrazones from a chiral 3-amino-2-oxazolidinone. J. Am. Chem. Soc. 122, 8329–8330 (2000).

Article  CAS  Google Scholar 

Friestad, G. K., Shen, Y. & Ruggles, E. L. Enantioselective radical addition to N-acyl hydrazones mediated by chiral Lewis acids. Angew. Chem. Int. Ed. 42, 5061–5063 (2003).

Article  CAS  Google Scholar 

Heinz, C. et al. Ni-catalyzed carbon–carbon bond-forming reductive amination. J. Am. Chem. Soc. 140, 2292–2300 (2018).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Presset, M. et al. CoI-catalyzed Barbier reactions of aromatic halides with aromatic aldehydes and imines. Chem. Eur. J. 25, 4491–4495 (2019).

Article  CAS  PubMed  Google Scholar 

Ni, S. et al. A general amino acid synthesis enabled by innate radical cross-coupling. Angew. Chem. Int. Ed. 57, 14560–14565 (2018).

Article  CAS  Google Scholar 

Turro, R. F., Brandstätter, M. & Reisman, S. E. Nickel-catalyzed reductive alkylation of heteroaryl imines. Angew. Chem. Int. Ed. 61, e202207597 (2022).

Article  CAS  Google Scholar 

Kumar, R., Flodén, N. J., Whitehurst, W. G. & Gaunt, M. J. A general carbonyl alkylative amination for tertiary amine synthesis. Nature 581, 415–420 (2020).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Blackwell, J. H., Kumar, R. & Gaunt, M. J. Visible-light-mediated carbonyl alkylative amination to all-alkyl α-tertiary amino acid derivatives. J. Am. Chem. Soc. 143, 1598–1609 (2021).

Article  CAS  PubMed  Google Scholar 

Subramanian, H., Landais, Y. & Sibi, M. P. in Comprehensive Organic Synthesis II (eds Knochel, P. & Molander, G. A.) 699–741 (Elsevier, 2014).

Li, Y., Lei, M. & Gong, L. Photocatalytic regio- and stereoselective C(sp3)–H functionalization of benzylic and allylic hydrocarbons as well as unactivated alkanes. Nat. Catal. 2, 1016–1026 (2019).

Article  CAS  Google Scholar 

Amatore, M. & Gosmini, C. Direct method for carbon–carbon bond formation: the functional group tolerant cobalt-catalyzed alkylation of aryl halides. Chem. Eur. J. 16, 5848–5852 (2010).

Article  CAS  PubMed  Google Scholar 

Gosmini, C. & Auffrant, A. in PATAI’S Chemistry of Functional Groups (Wiley, 2022).

Wang, L., Wang, L., Li, M., Chong, Q. & Meng, F. Cobalt-catalyzed diastereo- and enantioselective reductive allyl additions to aldehydes with allylic alcohol derivatives via allyl radical intermediates. J. Am. Chem. Soc. 143, 12755–12765 (2021).

Article  CAS  PubMed  Google Scholar 

Jiang, X. et al. Photoassisted cobalt-catalyzed asymmetric reductive Grignard-type addition of aryl iodides. J. Am. Chem. Soc. 144, 8347–8354 (2022).

Article  CAS  PubMed  Google Scholar 

Poremba, K. E., Dibrell, S. E. & Reisman, S. E. Nickel-catalyzed enantioselective reductive cross-coupling reactions. ACS Catal. 10, 8237–8246 (2020).

Article  CAS  PubMed  PubMed Central  Google Scholar 

Ortiz, E., Shezaf, J., Chang, Y.-H. & Krische, M. J. Enantioselective metal-catalyzed reductive coupling of alkynes with carbonyl compounds and imines: convergent construction of allylic alcohols and amines. ACS Catal. 12, 8164–8174 (2022).

Article  CAS