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Synlett 2021; 32(17): 1741-1746
DOI: 10.1055/a-1581-2345
DOI: 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
We thank the financial support from the National Natural Science Foundation of China (Grant No. 51373067).
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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
tert-leucine - 4-azaindolines - phase-transfer catalyst - enantiomers - intramolecular Mannich reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1581-2345.
- Supporting Information
Publication History
Received: 24 March 2021
Accepted after revision: 09 August 2021
Accepted Manuscript online:
09 August 2021
Article published online:
24 August 2021
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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.