Matsunaga, S. et al. Catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile eromoted by gallium heterobimetallic multifunctional complexes. J. Am. Chem. Soc. 122, 2252–2260 (2000).Article
CAS
Google Scholar
LaPlante, S. R. et al. Assessing atropisomer axial chirality in drug discovery and development. J. Med. Chem. 54, 7005–7022 (2011).Article
CAS
PubMed
Google Scholar
Zhu, Y.-Y., Wu, X.-D., Gu, S.-X. & Pu, L. Free amino acid recognition: a bisbinaphthyl-based fluorescent probe with high enantioselectivity. J. Am. Chem. Soc. 141, 175–181 (2019).Article
CAS
PubMed
Google Scholar
Fayez, S. et al. A near-complete series of four atropisomeric Jozimine A2-type naphthylisoquinoline dimers with antiplasmodial and cytotoxic activities and related alkaloids from Ancistrocladus abbreviatus. J. Nat. Prod. 82, 3033–3046 (2019).Article
CAS
PubMed
Google Scholar
Takaishi, K., Hinoide, S., Matsumoto, T. & Ema, T. Axially chiral peri-xanthenoxanthenes as a circularly polarized luminophore. J. Am. Chem. Soc. 141, 11852–11857 (2019).Article
CAS
PubMed
Google Scholar
Takaishi, K., Iwachido, K., Takehana, R., Uchiyama, M. & Ema, T. Evolving fluorophores into circularly polarized luminophores with a chiral naphthalene tetramer: proposal of excimer chirality rule for circularly polarized luminescence. J. Am. Chem. Soc. 141, 6185–6190 (2019).Article
CAS
PubMed
Google Scholar
Liu, C.-X. et al. Rhodium-catalyzed asymmetric C–H functionalization reactions. Chem. Rev. 123, 10079–10134 (2023).Article
ADS
CAS
PubMed
Google Scholar
Bao, X., Rodriguez, J. & Bonne, D. Enantioselective synthesis of atropisomers with multiple stereogenic axes. Angew. Chem. Int. Ed. 59, 12623–12634 (2020).Article
CAS
Google Scholar
Cheng, J. K., Xiang, S.-H., Li, S., Ye, L. & Tan, B. Recent advances in catalytic asymmetric construction of atropisomers. Chem. Rev. 121, 4805–4902 (2021).Article
CAS
PubMed
Google Scholar
Schmidt, T. A. & Sparr, C. Catalyst control over twofold and higher-order stereogenicity by atroposelective arene formation. Acc. Chem. Res. 54, 2764–2774 (2021).Article
CAS
PubMed
Google Scholar
Zhang, Z.-X., Zhai, T.-Y. & Ye, L.-W. Synthesis of axially chiral compounds through catalytic asymmetric reactions of alkynes. Chem Catal. 1, 1378–1412 (2021).Article
CAS
Google Scholar
Hayashi, T., Hayashizaki, K. & Ito, Y. Asymmetric synthesis of axially chiral 1,1′:5′,1″- and 1,1′:4′,1″- ternaphthalenes by asymmetric cross-coupling with a chiral ferrocenylphosphine-nickel catalyst. Tetrahedron. Lett. 30, 215–218 (1989).Article
CAS
Google Scholar
Shibata, T., Fujimoto, T., Yokota, K. & Takagi, K. Iridium complex-catalyzed highly enantio- and diastereoselective [2+2+2] cycloaddition for the synthesis of axially chiral teraryl compounds. J. Am. Chem. Soc. 126, 8382–8383 (2004).Article
CAS
PubMed
Google Scholar
Tanaka, K., Suda, T., Noguchi, K. & Hirano, M. Catalytic [2+2+2] and thermal [4+2] cycloaddition of 1,2-bis(arylpropiolyl)benzenes. J. Org. Chem. 72, 2243–2246 (2007).Article
CAS
PubMed
Google Scholar
Xu, G., Fu, W., Liu, G., Senanayake, C. H. & Tang, W. Efficient syntheses of Korupensamines A, B and Michellamine B by asymmetric Suzuki–Miyaura coupling reactions. J. Am. Chem. Soc. 136, 570–573 (2014).Article
CAS
PubMed
Google Scholar
Tan, Y. et al. Enantioselective construction of vicinal diaxial styrenes and multiaxis system via organocatalysis. J. Am. Chem. Soc. 140, 16893–16898 (2018).Article
CAS
PubMed
Google Scholar
Bisag, G. D. et al. Central‐to‐axial chirality conversion approach designed on organocatalytic enantioselective povarov cycloadditions: first access to configurationally stable indole-quinoline atropisomers. Chem. Eur. J. 25, 15694–15701 (2019).Article
CAS
PubMed
Google Scholar
Shen, D., Xu, Y. & Shi, S.-L. A bulky chiral N-heterocyclic carbene palladium catalyst enables highly enantioselective Suzuki–Miyaura cross-coupling reactions for the synthesis of biaryl atropisomers. J. Am. Chem. Soc. 141, 14938–14945 (2019).Article
CAS
PubMed
Google Scholar
Bao, X., Rodriguez, J. & Bonne, D. Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C–C stereogenic axes. Chem. Sci. 11, 403–408 (2020).Article
CAS
PubMed
Google Scholar
Beleh, O. M., Miller, E., Toste, F. D. & Miller, S. J. Catalytic dynamic kinetic resolutions in tandem to construct two-axis terphenyl atropisomers. J. Am. Chem. Soc. 142, 16461–16470 (2020).Article
CAS
PubMed
PubMed Central
Google Scholar
Nguyen, Q.-H., Guo, S.-M., Royal, T., Baudoin, O. & Cramer, N. Intermolecular palladium(0)-catalyzed atropo-enantioselective C–H arylation of heteroarenes. J. Am. Chem. Soc. 142, 2161–2167 (2020).Article
CAS
PubMed
Google Scholar
Xia, W. et al. Chiral phosphoric acid catalyzed atroposelective C–H amination of arenes. Angew. Chem. Int. Ed. 59, 6775–6779 (2020).Article
CAS
Google Scholar
Liao, G. et al. Experimental and computational studies on the directing ability of chalcogenoethers in palladium-catalyzed atroposelective C–H olefination and allylation. Angew. Chem. Int. Ed. 61, e202115221 (2022).Article
CAS
Google Scholar
Wang, Y. et al. Rhodium-catalyzed enantioselective and diastereodivergent access to diaxially chiral heterocycles. Nat. Commun. 14, 4661 (2023).Article
ADS
CAS
PubMed
PubMed Central
Google Scholar
Shibata, T., Tsuchikama, K. & Otsuka, M. Enantioselective intramolecular [2+2+2] cycloaddition of triynes for the synthesis of atropisomeric chiral ortho-diarylbenzene derivatives. Tetrahedron: Asymmetry 17, 614–619 (2006).Article
CAS
Google Scholar
Barrett, K. T., Metrano, A. J., Rablen, P. R. & Miller, S. J. Spontaneous transfer of chirality in an atropisomerically enriched two-axis system. Nature 509, 71–75 (2014).Article
ADS
CAS
PubMed
PubMed Central
Google Scholar
Moser, D. & Sparr, C. Synthesis of atropisomeric two-axis systems by the catalyst-controlled syn- and anti-selective arene-forming aldol condensation. Angew. Chem. Int. Ed. 61, e202202548 (2022).Article
ADS
CAS
Google Scholar
Zhang, X.-L. et al. Stepwise asymmetric allylic substitution-isomerization enabled mimetic synthesis of axially chiral B, N‐heterocycles. Angew. Chem. Int. Ed. 61, e202210456 (2022).Article
CAS
Google Scholar
Han, T.-J. et al. Catalytic atroposelective synthesis of heterobiaryls with vicinal C–C and N–N diaxes via dynamic kinetic resolution. iScience 26, 107978 (2023).Article
ADS
CAS
PubMed
PubMed Central
Google Scholar
Zhang, S.-C. et al. Enantioselective access to triaryl-2-pyrones with monoaxial or contiguous C–C diaxes via oxidative NHC catalysis. ACS Catal. 13, 2565–2575 (2023).Article
CAS
Google Scholar
Oppenheimer, J., Hsung, R. P., Figueroa, R. & Johnson, W. L. Stereochemical control of both C–C and C–N axial chirality in the synthesis of chiral N,O-biaryls. Org. Lett. 9, 3969–3972 (2007).Article
CAS
PubMed
Google Scholar
Lotter, D., Neuburger, M., Rickhaus, M., Häussinger, D. & Sparr, C. Stereoselective arene-forming aldol condensation: synthesis of configurationally stable oligo-1,2-naphthylenes. Angew. Chem. Int. Ed. 55, 2920–2923 (2016).Article
CAS
Google Scholar
Dherbassy, Q., Djukic, J. P., Wencel-Delord, J. & Colobert, F. Two stereoinduction events in one C–H activation step: a route towards terphenyl ligands with two atropisomeric axes. Angew. Chem. Int. Ed. 57, 4668–4672 (2018).Article
CAS
Google Scholar
Hu, Y.-L. et al. Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3–diarylbenzoindoles. Chem. Sci. 10, 6777–6784 (2019).Article
CAS
PubMed
PubMed Central
Google Scholar
Wang, B.-J. et al. Single-step synthesis of atropisomers with vicinal C–C and C–N diaxes by cobalt-catalyzed atroposelective C–H annulation. Angew. Chem. Int. Ed. 61, e202208912 (2022).Article
ADS
CAS
Google Scholar
Zhang, S. et al. Atroposelective synthesis of triaryl α-pyranones with 1,2-diaxes by N-heterocyclic carbene organocatalysis. Angew. Chem. Int. Ed. 61, e202212005 (2022).Article
CAS
Google Scholar
Luc, A. et al. Double cobalt-catalyzed atroposelective C–H activation: one-step synthesis of atropisomeric indoles bearing vicinal C–C and C–N diaxes. Chem. Catal. 3, 100765 (2023).Article
CAS
Google Scholar
Yang, K. et al. Construction of C–B axial chirality via dynamic kinetic asymmetric cross-coupling mediated by tetracoordinate boron. Nat. Commun. 14, 4438 (2023).Article
ADS
CAS
PubMed
PubMed Central
Google Scholar
Gao, Q. et al. Catalytic synthesis of atropisomeric o-terphenyls with 1,2-diaxes via axial-to-axial diastereoinduction. J. Am. Chem. Soc. 143, 7253–7260 (2021).Article
CAS
PubMed
Google Scholar
Wang, Y.-B. & Tan, B. Construction of axially chiral compounds via asymmetric organocatalysis. Acc. Chem. Res. 51, 534–547 (2018).Article
CAS
PubMed
Google Scholar
Kitagawa, O. Chiral Pd-catalyzed enantioselective syntheses of various N–C axially chiral compounds and their synthetic applications. Acc. Chem. Res. 54, 719–730 (2021).Article
CAS
PubMed
Google Scholar
Wu, Y.-J., Liao, G. & Shi, B.-F. Stereoselective construction of atropisomers featuring a C–N chiral axis. Green Synth. Catal. 3, 117–136 (2022).Article
Google Scholar
Cai, W.-Y., Ding, Q.-N., Zhou, L. & Chen, J. Asymmetric synthesis of axially chiral molecules via organocatalytic cycloaddition and cyclization reactions. Molecules 28, 4306 (2023).Article
CAS
PubMed
PubMed Central
Google Scholar
Chen, Y.-B., Yang, Y.-N., Huo, X.-Z., Ye, L.-W. & Zhou, B. Recent advances in the construction of axially chiral arylpyrroles. Sci. China Chem. 66, 2480–2491 (2023).Article
CAS
Google Scholar
Faisca Phillips, A. M. & Pombeiro, A. J. L. Atropselective organocatalytic synthesis of chiral compounds containing nitrogen along the axis of chirality. Symmetry 15, 1261 (2023).Article
ADS
CAS
Google Scholar
Zhang, L. et al. Phosphoric acid-catalyzed atroposelective construction of axially chiral arylpyrroles. Nat. Commun. 10, 566 (2019).Article
ADS
PubMed
PubMed Central
Google Scholar
Zhang, S. et al. Enantioselective synthesis of atropisomers featuring pentatomic heteroaromatics by Pd-catalyzed C–H alkynylation. ACS Catal 9, 1956–1961 (2019).Article
CAS
Google Scholar
Wang, X.-M. et al. Enantioselective synthesis of nitrogen-nitrogen biaryl atropisomers via copper-catalyzed Friedel–Crafts alkylation reaction. J. Am. Chem. Soc. 143, 15005–15010 (2021).Article
CAS
PubMed
Google Scholar
Yin, S.-Y., Zhou, Q., Liu, C.-X., Gu, Q. & You, S.-L. Enantioselective synthesis of N–N biaryl atropisomers through iridium(I)-catalyzed C–H alkylation with acrylates. Angew. Chem. Int. Ed. 62, e202305067 (2023).Article
CAS
Google Scholar
Zhang, L., Zhang, J., Ma, J., Cheng, D.-J. & Tan, B. Highly atroposelective synthesis of arylpyrroles by catalytic asymmetric Paal–Knorr reaction. J. Am. Chem. Soc. 139, 1714–1717 (2017).Article
CAS
PubMed
Google Scholar
He, X.-L. et al. Asymmetric Barton–Zard reaction to access 3-pyrrole-containing axially chiral skeletons. ACS Catal 9, 4374–4381 (2019).Article
CAS
Google Scholar
Wang, Y.-B. et al. Asymmetric construction of axially chiral 2-arylpyrroles by chirality transfer of atropisomeric alkenes. Angew. Chem. Int. Ed. 58, 13443–13447 (2019).Article
CAS
Google Scholar
Zheng, S.-C., Wang, Q. & Zhu, J. Catalytic kinetic resolution by enantioselective aromatization: conversion of racemic intermediates of the Barton–Zard reaction into enantioenriched 3-arylpyrroles. Angew. Chem. Int. Ed. 58, 9215–9219 (2019).Article
CAS
Google Scholar
Xu, Q. et al. Cu(I)-catalyzed asymmetric arylation of pyrroles with diaryliodonium salts toward the synthesis of N−N atropisomers. Org. Lett. 24, 3138–3143 (2022).Article
CAS
PubMed
Google Scholar
Han, T.-J., Zhang, Z.-X., Wang, M.-C., Xu, L.-P. & Mei, G.-J. The rational design and atroposelective synthesis of axially chiral C2-arylpyrrole-derived amino alcohols. Angew. Chem. Int. Ed. 61, e202207517 (2022).Article
ADS
CAS
Google Scholar
Tan, C. X. A. et al. Synthesis of axially chiral CF3-substituted 2-arylpyrroles by sequential phosphine-catalyzed asymmetric [3+2] annulation and oxidative central-to-axial chirality transfer. Angew. Chem. Int. Ed. 61, e202209494 (2022).Article
Google Scholar
Zhao, Y., Liu, N., Zhong, S., Wen, Z. & Wang, T. A central-to-axial chirality conversion strategy for the synthesis of C-N axially chiral N-arylpyrroles. Org. Lett. 24, 2842–2846 (2022).Article
CAS
PubMed
Google Scholar
Chen, Y.-B. et al. Construction of axially chiral arylpyrroles via atroposelective diyne cyclization. Angew. Chem. Int. Ed. 62, e202303670 (2023).Article
ADS
CAS
Google Scholar
Man, N. et al. Organocatalytic atroposelective construction of axially chiral N-aryl benzimidazoles involving carbon-carbon bond cleavage. Org. Lett. 22, 6382–6387 (2020).Article
CAS
PubMed
Google Scholar
An, Q.-J. et al. Nitrosobenzene-enabled chiral phosphoric acid catalyzed enantioselective construction of atropisomeric N-arylbenzimidazoles. Angew. Chem. Int. Ed. 60, 24888–24893 (2021).Article
CAS
Google Scholar
Sun, L. et al. Rhodium-catalyzed atroposelective construction of indoles via C–H bond activation. Angew. Chem. Int. Ed. 60, 8391–8395 (2021).Article
CAS
Google Scholar
Yang, G. et al. Organocatalytic higher-order [8+2] cycloaddition for the assembly of atropoenantiomeric 3-arylindolizines. Org. Lett. 23, 8109–8113 (2021).Article
CAS
PubMed
Google Scholar
Wang, Y. et al. Construction of axially chiral indoles by cycloaddition-isomerization via atroposelective phosphoric acid and silver sequential catalysis. ACS Catal 12, 8094–8103 (2022).Article
CAS
Google Scholar
Wang, Z.-S. et al. Synthesis of axially chiral N-arylindoles via atroposelective cyclization of ynamides catalyzed by chiral brønsted acids. Angew. Chem. Int. Ed. 61, e202201436 (2022).Article
ADS
CAS
Google Scholar
Zhang, P. et al. Enantioselective synthesis of N–N bisindole atropisomers. Angew. Chem. Int. 61, e202212101 (2022).Article
ADS
CAS
Google Scholar
Thies, N. & Haak, E. Ruthenium-catalyzed synthesis of 2,3-cyclo[3]dendralenes and complex polycycles from propargyl alcohols. Angew. Chem. Int. Ed. 54, 4097–4101 (2015).Article
CAS
Google Scholar
Kong, H.-H. et al. Remote enantioselective [4+1] annulation with copper-vinylvinylidene intermediates. J. Am. Chem. Soc. 144, 21347–21355 (2022).Article
CAS
PubMed
Google Scholar
Ma, J.-S. et al. Copper-catalysed convergent regio- and enantioselective alkynylallylic substitution. Nat. Synth. 2, 37–48 (2022).Article
ADS
Google Scholar
Niu, S. et al. Copper-catalyzed yne-allylic substitutions using stabilized nucleophiles. ACS Catal 12, 6840–6850 (2022).Article
CAS
Google Scholar
Li, M.-D. et al. Copper-catalyzed remote enantioselective sulfonylation of yne-allylic esters with sodium sulfinates. Angew. Chem. Int. Ed. 62, e202313911 (2023).Article
ADS
CAS
Google Scholar
Luo, D. et al. Copper-catalyzed asymmetric yne-allylic substitution using electron-rich arenes. ACS Catal 14, 2746–2757 (2024).Article
CAS
Google Scholar
Sun, Y.-Z. et al. Asymmetric substitution by alkynyl copper driven dearomatization and rearomatization. Angew. Chem. Int. Ed. 62, e202314517 (2023).Article
CAS
Google Scholar
Qian, H.-D. et al. Remote copper-catalyzed enantioselective substitution of yne-thiophene carbonates. Sci. China Chem. 67, 1175–1180 (2024).Article
CAS
Google Scholar
Zhang, Z. et al. Enantioselective propargylic amination and related tandem sequences to α-tertiary ethynylamines and azacycles. Nat. Chem. 16, 521–532 (2024).Article
ADS
CAS
PubMed
Google Scholar
Trost, B. M., Machacek, M. R. & Aponick, A. Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model. Acc. Chem. Res. 39, 747–760 (2006).Article
CAS
PubMed
Google Scholar
Cheng, Q. et al. Iridium-catalyzed asymmetric allylic substitution reactions. Chem. Rev. 119, 1855–1969 (2019).Article
ADS
CAS
PubMed
Google Scholar
Liu, S.-J. et al. Rational design of axially chiral styrene-based organocatalysts and their application in catalytic asymmetric (2+4) cyclizations. Angew. Chem. Int. Ed. 61, e202112226 (2022).Article
ADS
CAS
Google Scholar