Synlett, Table of Contents Synlett 2021; 32(17): 1741-1746DOI: 10.1055/a-1581-2345 letter Asymmetric Synthesis of 3-Phenyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-3-carbonitriles Catalyzed by Phase-Transfer Catalyst Derived from tert-Leucine Zhiqi Zhao , Jingdong Wang , Zhonglin Wei , Jungang Cao , Dapeng Liang , Haifeng Duan∗ , Yingjie Lin∗Recommend Article Abstract Buy Article All articles of this category Abstract Chiral phase-transfer catalysts derived from tert-leucine were synthesized and used in the asymmetric synthesis of 4-azaindoline derivatives. By this method, both enantiomers of the corresponding products were obtained in excellent yield (up to 99%) with high enantioselectivities (up to 91% ee) and diastereoselectivities (up to >99: 1 dr). Key words Key words tert-leucine - 4-azaindolines - phase-transfer catalyst - enantiomers - intramolecular Mannich reaction Full Text References References 1 Wang H, Zheng C, Zhao G. Chin. J. Chem. 2019; 37: 1111 2 Chai Z, Zhao G. Catal. Sci. Technol. 2012; 2: 29 3 Zhang X.-X, Gao Y, Hu X.-S, Ji C.-B, Liu Y.-L, Yu J.-S. Adv. Synth. Catal. 2020; 362: 4763 4 Wang H, Wang K, Man Y, Gao X, Yang L, Ren Y, Li N, Tang B, Zhao G. Adv. Synth. Catal. 2017; 359: 3934 5 Pan R, Zhang J, Zheng C, Wang H, Cao D, Cao W, Zhao G. Tetrahedron 2017; 73: 2349 6 Wang Y, Cobo AA, Franz AK. Org. Chem. Front. 2021; 8: 4315 7 Liu Y, Wei Z, Liu Y, Cao J, Liang D, Lin Y, Duan H. Org. Biomol. Chem. 2017; 15: 9234 8 Liu Y, Wei Z, Liu Y, Wang J, Cao J, Liang D, Duan H, Lin Y. Chem. Res. Chin. Univ. 2018; 34: 333 9 Piatnitski Chekler EL, Khan TA, Mamidala R, Anderson JT, Tangirala RS, Verhoest PR, Gilbert AM. Tetrahedron Lett. 2012; 53: 377 10 Gerken PA, Wolstenhulme JR, Tumber A, Hatch SB, Zhang Y, Müller S, Chandler SA, Mair B, Li F, Nijman SM. B, Konietzny R, Szommer T, Yapp C, Fedorov O, Benesch JL. P, Vedadi M, Kessler BM, Kawamura A, Brennan PE, Smith MD. Angew. Chem. Int. Ed. 2017; 56: 15555 11 Nuhant P, Allais C, Chen MZ, Coe JW, Dermenci A, Fadeyi OO, Flick AC, Mousseau JJ. Org. Lett. 2015; 17: 4292 12 Maciver EE, Thompson S, Smith MD. Angew. Chem. Int. Ed. 2009; 48: 9979 13 Sharma K, Wolstenhulme JR, Painter PP, Yeo D, Grande-Carmona F, Johnston CP, Tantillo DJ, Smith MD. J. Am. Chem. Soc. 2015; 137: 13414 14 Lamb AD, Davey PD, Driver RW, Thompson AL, Smith MD. Org. Lett. 2016; 18: 5372 15 Wang J, Liu Y, Wei Z, Cao J, Liang D, Lin Y, Duan H. J. Org. Chem. 2020; 85: 4047 16 Wang J, Liu Y, Liu Y, Wei Z, Cao J, Liang D, Lin Y, Duan H. Tetrahedron 2019; 75: 2883 17 CCDC 2035962 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures. Supplementary Material Supplementary Material Supporting Information