Synthesis, Table of Contents CC BY-NC-ND 4.0 · Synthesis 2023; 55(11): 1770-1782DOI: 10.1055/a-1993-6899 paper Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award Control over Stereogenic N–N Axes by Pd-Catalyzed 5-endo-Hydroaminocyclizations Valeriia Hutskalova , Christof Sparr ∗Recommend Article Abstract All articles of this category Dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award Abstract A novel approach for the stereoselective construction of N–N atropisomeric compounds by a Pd-catalyzed 5-endo-hydroaminocyclization is described herein. A broad range of bisheterocycles , connected by a configurationally stable N–N stereogenic axis, were prepared with catalyst control in enantioenriched form. Key words Key wordspalladium - cyclization - heterocycles - asymmetric catalysis - alkynes - atropisomers Full Text References References 1a Clayden J, Moran WJ, Edwards PJ, Laplante SR. Angew. Chem. Int. Ed. 2009; 48: 6398 1b Glunz PW. Bioorg. Med. Chem. Lett. 2018; 28: 53 1c Toenjes ST, Gustafson JL. Future Chem. 2018; 10: 409 2a Bringmann G, Gulder T, Gulder TA. M, Breuning M. Chem. Rev. 2011; 111: 563 2b Wencel-Delord J, Panossian A, Leroux FR, Colobert F. Chem. Soc. Rev. 2015; 44: 3418 2c Zilate B, Castrogiovanni A, Sparr C. ACS Catal. 2018; 8: 2981 3 Gustafson JL, Lim D, Miller SJ. Science 2010; 328: 1251 4 Wang JZ, Zhou J, Xu C, Sun H, Kürti L, Xu QL. J. Am. Chem. Soc. 2016; 138: 5202 5 Rokade BV, Guiry PJ. ACS Catal. 2018; 8: 624 6 Sweetman BA, Guiry PJ. Tetrahedron 2018; 74: 5567 7 Zhang P, Wang XM, Xu Q, Guo CQ, Wang P, Lu CJ, Liu RR. Angew. Chem. Int. Ed. 2021; 60: 21718 8 Rodríguez-Salamanca P, Fernández R, Hornillos V, Lassaletta JM. Chem. Eur. J. 2022; 28: e202104442 9 Di Iorio N, Righi P, Mazzanti A, Mancinelli M, Ciogli A, Bencivenni G. J. Am. Chem. Soc. 2014; 136: 10250 10 Hirai M, Terada S, Yoshida H, Ebine K, Hirata T, Kitagawa O. Org. Lett. 2016; 18: 5700 11 Bai HY, Tan FX, Liu TQ, Zhu GD, Tian JM, Ding TM, Chen ZM, Zhang SY. Nat. Commun. 2019; 10: 3063 12 Frey J, Malekafzali A, Delso I, Choppin S, Colobert F, Wencel-Delord J. Angew. Chem. Int. Ed. 2020; 59: 8844 13 Vaidya SD, Toenjes ST, Yamamoto N, Maddox SM, Gustafson JL. J. Am. Chem. Soc. 2020; 142: 2198 14 Chang C, Adams R. J. Am. Chem. Soc. 1931; 53: 2353 15a Xu Z, Baunach M, Ding L, Hertweck C. Angew. Chem. Int. Ed. 2012; 51: 10293 15b Zhang Q, Mándi A, Li S, Chen Y, Zhang W, Tian X, Zhang H, Li H, Zhang W, Zhang S, Ju J, Kurtán T, Zhang C. Eur. J. Org. Chem. 2012; 2012: 5256 16a Dai J, Dan W, Schneider U, Wang J. Eur. J. Med. Chem. 2018; 157: 622 16b Blair LM, Sperry J. J. Nat. Prod. 2013; 76: 794 17 Liu XY, Zhang YL, Fei X, Liao LS, Fan J. Chem. Eur. J. 2019; 25: 4501 18 Antognazza P, Benincori T, Mazzoli S, Sannicolo F, Pilati T. Phosphorus, Sulfur Silicon Relat. Elem. 1999; 146: 405 19 Mei GJ, Wong JJ, Zheng W, Nangia AA, Houk KN, Lu Y. Chem 2021; 7: 2743 20 Lin W, Zhao Q, Li Y, Pan M, Yang C, Yang GH, Li X. Chem. Sci. 2022; 13: 141 21 Pan M, Shao YB, Zhao Q, Li X. Org. Lett. 2022; 24: 374 22a Xu Q, Zhang H, Ge FB, Wang XM, Zhang P, Lu CJ, Liu RR. Org. Lett. 2022; 24: 3138 22b Wang XM, Zhang P, Xu Q, Guo CQ, Zhang DB, Lu CJ, Liu RR. J. Am. Chem. Soc. 2021; 143: 15005 23a Gao Y, Wang LY, Zhang T, Yang BM, Zhao Y. Angew. Chem. Int. Ed. 2022; 61: e202200371 23b Chen KW, Chen ZH, Yang S, Wu SF, Zhang YC, Shi F. Angew. Chem. Int. Ed. 2022; 61: e202116829 24a Portolani C, Centonze G, Luciani S, Pellegrini A, Righi P, Mazzanti A, Ciogli A, Sorato A, Bencivenni G. Angew. Chem. Int. Ed. 2022; 61: e202209895 24b Zhang P, Wang X.-M, Feng J, Lu C.-J, Li Y, Liu RR. Angew. Chem. Int. Ed. 2022; 61: e202212101 25a Ototake N, Morimoto Y, Mokuya A, Fukaya H, Shida Y, Kitagawa O. Chem. Eur. J. 2010; 16: 6752 25b Morimoto Y, Shimizu S, Mokuya A, Ototake N, Saito A, Kitagawa O. Tetrahedron 2016; 72: 5221 26a Alsabeh PG, Lundgren RJ, Longobardi LE, Stradiotto M. Chem. Commun. 2011; 47: 6936 26b Halland N, Nazare M, Alonso J, R’Kyek O, Lindenschmidt A. Chem. Commun. 2011; 47: 1042 Supplementary Material Supplementary Material Supporting Information CIF File