Carreira, E. M. & Yamamoto, H. Comprehensive Chirality (Elsevier, 2012).Anthonsen, T. Chiral Drugs: Chemistry and Biological Action (Wiley, 2011).Geist, E., Kirschning, A. & Schmidt, T. sp3–sp3 coupling reactions in the synthesis of natural products and biologically active molecules. Nat. Prod. Rep. 31, 441–448 (2014).Article
CAS
PubMed
Google Scholar
Lovering, F., Bikker, J. & Humblet, C. Escape from flatland: increasing saturation as an approach to improving clinical success. J. Med. Chem. 52, 6752–6756 (2009).Article
CAS
PubMed
Google Scholar
Baruah, B. & Deb, M. L. Alkylation of electron-deficient olefins through conjugate addition of organozinc reagents: an update. Eur. J. Org. Chem. 2021, 5756–5766 (2021).Article
CAS
Google Scholar
Chen, Z. et al. Catalytic alkylation of unactivated C(sp3)–H bonds for C(sp3)–C(sp3) bond formation. Chem. Soc. Rev. 48, 4921–4942 (2019).Article
CAS
PubMed
Google Scholar
Fu, G. C. Transition-metal catalysis of nucleophilic substitution reactions: a radical alternative to SN1 and SN2 processes. ACS Cent. Sci. 3, 692–700 (2017).Article
CAS
PubMed
PubMed Central
Google Scholar
Kranthikumar, R. Recent advances in C(sp3)–C(sp3) cross-coupling chemistry: a dominant performance of nickel catalysts. Organometallics 41, 667–679 (2022).Article
CAS
Google Scholar
Cherney, A. H., Kadunce, N. T. & Reisman, S. E. Enantioselective and enantiospecific transition-metal-catalyzed cross-coupling reactions of organometallic reagents to construct C–C bonds. Chem. Rev. 115, 9587–9652 (2015).Article
CAS
PubMed
PubMed Central
Google Scholar
Choi, J. & Fu, G. C. Transition metal-catalyzed alkyl–alkyl bond formation: another dimension in cross-coupling chemistry. Science 356, eaaf7230 (2017).Article
PubMed
PubMed Central
Google Scholar
Zultanski, S. L. & Fu, G. C. Catalytic asymmetric γ-alkylation of carbonyl compounds via stereoconvergent Suzuki cross-couplings. J. Am. Chem. Soc. 133, 15362–15364 (2011).Article
CAS
PubMed
PubMed Central
Google Scholar
Wilsily, A., Tramutola, F., Owston, N. A. & Fu, G. C. New directing groups for metal-catalyzed asymmetric carbon–carbon bond-forming processes: stereoconvergent alkyl–alkyl Suzuki cross-couplings of unactivated electrophiles. J. Am. Chem. Soc. 134, 5794–5797 (2012).Article
CAS
PubMed
PubMed Central
Google Scholar
Schmidt, J. et al. A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters. Science 354, 1265–1269 (2016).Article
CAS
PubMed
PubMed Central
Google Scholar
Huo, H. H., Gorsline, B. J. & Fu, G. C. Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles. Science 367, 559–564 (2020).Article
CAS
PubMed
PubMed Central
Google Scholar
Schwarzwalder, G. M., Matier, C. D. & Fu, G. C. Enantioconvergent cross-couplings of alkyl electrophiles: the catalytic asymmetric synthesis of organosilanes. Angew. Chem. Int. Ed. 58, 3571–3574 (2019).Article
CAS
Google Scholar
Tong, X., Schneck, F. & Fu, G. C. Catalytic enantioselective α-alkylation of amides by unactivated alkyl electrophiles. J. Am. Chem. Soc. 144, 14856–14863 (2022).Article
CAS
PubMed
PubMed Central
Google Scholar
Lu, X. et al. Practical carbon–carbon bond formation from olefins through nickel-catalyzed reductive olefin hydrocarbonation. Nat. Commun. 7, 11129 (2016).Article
PubMed
PubMed Central
Google Scholar
Wang, Z., Yin, H. & Fu, G. C. Catalytic enantioconvergent coupling of secondary and tertiary electrophiles with olefins. Nature 563, 379–383 (2018).Article
CAS
PubMed
PubMed Central
Google Scholar
Zhou, F., Zhang, Y., Xu, X. & Zhu, S. NiH-catalyzed remote asymmetric hydroalkylation of alkenes with racemic α-bromo amides. Angew. Chem. Int. Ed. 58, 1754–1758 (2019).Article
CAS
Google Scholar
He, S.-J. et al. Nickel-catalyzed enantioconvergent reductive hydroalkylation of olefins with α-heteroatom phosphorus or sulfur alkyl electrophiles. J. Am. Chem. Soc. 142, 214–221 (2020).Article
CAS
PubMed
Google Scholar
Yang, Z.-P. & Fu, G. C. Convergent catalytic asymmetric synthesis of esters of chiral dialkyl carbinols. J. Am. Chem. Soc. 142, 5870–5875 (2020).Article
CAS
PubMed
PubMed Central
Google Scholar
Shi, L., Xing, L.-L., Hu, W.-B. & Shu, W. Regio- and enantioselective Ni-catalyzed formal hydroalkylation, hydrobenzylation and hydropropargylation of acrylamides to α-tertiary amides. Angew. Chem. Int. Ed. 60, 1599–1604 (2021).Article
CAS
Google Scholar
Bera, S., Mao, R. & Hu, X. Enantioselective C(sp3)–C(sp3) cross-coupling of non-activated alkyl electrophiles via nickel hydride catalysis. Nat. Chem. 13, 270–277 (2021).Article
CAS
PubMed
Google Scholar
Qian, D., Bera, S. & Hu, X. Chiral alkyl amine synthesis via catalytic enantioselective hydroalkylation of enecarbamates. J. Am. Chem. Soc. 143, 1959–1967 (2021).Article
CAS
PubMed
Google Scholar
Sun, S.-Z. et al. Enantioselective deaminative alkylation of amino acid derivatives with unactivated olefins. J. Am. Chem. Soc. 144, 1130–1137 (2022).Article
CAS
PubMed
Google Scholar
Wang, J.-W. et al. Catalytic asymmetric reductive hydroalkylation of enamides and enecarbamates to chiral aliphatic amines. Nat. Commun. 12, 1313 (2021).Article
CAS
PubMed
PubMed Central
Google Scholar
Zhou, F. & Zhu, S. Catalytic asymmetric hydroalkylation of α,β-unsaturated amides enabled by regio-reversed and enantiodifferentiating syn-hydronickellation. ACS Catal. 11, 8766–8773 (2021).Article
CAS
Google Scholar
Yang, P.-F. et al. Regio- and enantioselective hydroalkylations of unactivated olefins enabled by nickel catalysis: reaction development and mechanistic insights. ACS Catal. 12, 5795–5805 (2022).Article
CAS
Google Scholar
Huang, Q. et al. Nickel-hydride-catalyzed diastereo- and enantioselective hydroalkylation of cyclopropenes. Angew. Chem. Int. Ed. 61, e202210560 (2022).Article
CAS
Google Scholar
Li, Y. et al. Cobalt-catalysed enantioselective C(sp3)–C(sp3) coupling. Nat. Catal. 4, 901–911 (2021).Article
CAS
Google Scholar
Zhang, Z.-L. et al. Cobalt-catalyzed facial-selective hydroalkylation of cyclopropenes. Angew. Chem. Int. Ed. 62, e202306381 (2023).Article
CAS
Google Scholar
Zhang, Z., Bera, S., Fan, C. & Hu, X. Streamlined alkylation via nickel-hydride-catalyzed hydrocarbonation of alkenes. J. Am. Chem. Soc. 144, 7015–7029 (2022).Article
CAS
PubMed
Google Scholar
Yang, P.-F. & Shu, W. Asymmetric alkyl–alkyl cross-coupling enabled by earth-abundant metal-catalyzed hydroalkylations of olefins. Chem Catal. 3, 100508 (2023).Article
CAS
Google Scholar
Cherney, A. H., Kadunce, N. T. & Reisman, S. E. Catalytic asymmetric reductive acyl cross-coupling: synthesis of enantioenriched acyclic α,α-disubstituted ketones. J. Am. Chem. Soc. 135, 7442–7445 (2013).Article
CAS
PubMed
Google Scholar
Cherney, A. H. & Reisman, S. E. Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles. J. Am. Chem. Soc. 136, 14365–14368 (2014).Article
CAS
PubMed
PubMed Central
Google Scholar
Kadunce, N. T. & Reisman, S. E. Nickel-catalyzed asymmetric reductive cross-coupling between heteroaryl iodides and α-chloronitriles. J. Am. Chem. Soc. 137, 10480–10483 (2015).Article
CAS
PubMed
PubMed Central
Google Scholar
Poremba, K. E., Kadunce, N. T., Suzuki, N., Cherney, A. H. & Reisman, S. E. Nickel-catalyzed asymmetric reductive cross-coupling to access 1,1-diarylalkanes. J. Am. Chem. Soc. 139, 5684–5687 (2017).Article
CAS
PubMed
PubMed Central
Google Scholar
Hofstra, L., Cherney, A. H., Ordner, C. M. & Reisman, S. E. Synthesis of enantioenriched allylic silanes via nickel-catalyzed reductive cross-coupling. J. Am. Chem. Soc. 140, 139–142 (2018).Article
CAS
PubMed
Google Scholar
Guan, H., Zhang, Q., Walsh, P. J. & Mao, J. Nickel/photoredox-catalyzed asymmetric reductive cross-coupling of racemic α-chloro esters with aryl iodides. Angew. Chem. Int. Ed. 59, 5172–5177 (2020).Article
CAS
Google Scholar
Kang, K. & Weix, D. J. Nickel-catalyzed C(sp3)–C(sp3) cross-electrophile coupling of in situ generated NHP esters with unactivated alkyl bromides. Org. Lett. 24, 2853–2857 (2022).Article
CAS
PubMed
PubMed Central
Google Scholar
Liu, D. et al. Paired electrolysis-enabled nickel-catalyzed enantioselective reductive cross-coupling between α-chloroesters and aryl bromides. Nat. Commun. 13, 7318 (2022).Article
CAS
PubMed
PubMed Central
Google Scholar
Zhao, W.-T., Zhang, J.-X., Chen, B.-H. & Shu, W. Ligand-enabled Ni-catalysed enantioconvergent intermolecular alkyl–alkyl cross-coupling between distinct alkyl halides. Nat. Commun. 14, 2938 (2023).Article
CAS
PubMed
PubMed Central
Google Scholar
Zhao, W.-T. & Shu, W. Enantioselective Csp3–Csp3 formation by nickel-catalyzed cross-electrophile enantioconvergent alkyl–alkyl coupling of unactivated alkyl halides. Sci. Adv. 9, eadg9898 (2023).Article
CAS
PubMed
PubMed Central
Google Scholar
Yang, K. S., Gurak, J. A. Jr & Engle, K. M. Catalytic, regioselective hydrocarbofunctionalization of unactivated alkenes with diverse C–H nucleophiles. J. Am. Chem. Soc. 138, 14705–14712 (2016).Article
CAS
PubMed
Google Scholar
Yan, T. & Guironnet, D. Combination of olefin insertion polymerization and olefin metathesis to extend the topology and composition of polyolefins. Sci. China Chem. 63, 755–757 (2020).Article
CAS
Google Scholar
Wang, S. et al. Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations. Nat. Commun. 12, 2771 (2021).Article
CAS
PubMed
PubMed Central
Google Scholar
Yang, P.-F. & Shu, W. Orthogonal access to α-/β-branched/linear aliphatic amines by catalyst-tuned regiodivergent hydroalkylations. Angew. Chem. Int. Ed. 61, e202208018 (2022).Article
CAS
Google Scholar
Cheng, L., Liu, J., Chen, Y. & Gong, H. Nickel-catalysed hydrodimerization of unactivated terminal alkenes. Nat. Synth. 2, 364–372 (2023).Article
Google Scholar
Lo, J. C., Gui, J., Yabe, Y., Pan, C.-M. & Baran, P. S. Functionalized olefin cross-coupling to construct carbon–carbon bonds. Nature 516, 343–348 (2014).Article
CAS
PubMed
PubMed Central
Google Scholar
Lo, J. C., Yabe, Y. & Baran, P. S. A practical and catalytic reductive olefin coupling. J. Am. Chem. Soc. 136, 1304–1307 (2014).Article
CAS
PubMed
PubMed Central
Google Scholar
Wang, Y. et al. Copper-catalyzed asymmetric conjugate addition of alkene-derived nucleophiles to alkenyl-substituted heteroarenes. ACS Catal. 12, 9611–9620 (2022).Article
CAS
Google Scholar
Jang, W. J., Woo, J. & Yun, J. Asymmetric conjugate addition of chiral secondary borylalkyl copper species. Angew. Chem. Int. Ed. 60, 4614–4618 (2021).Article
CAS
Google Scholar