Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives

Scholarly Works

• Prasad, V. S.; Ranga Rao, V.; Gangadhar, M.; Nechipadappu, S. K.; Adiyala, P. R. Regioselective Radical Cascade Cyclizations of Alkyne-Tethered Cyclohexadienones with Chalcogenides under Visible-Light Catalysis. ACS omega 2023, 8, 35809–35821. doi:10.1021/acsomega.3c03362
• Liang, K.; Hua, R.; Yin, H.; Chen, F.-X. Me3SiCl-catalyzed tandem thiocyanation/cyclization of tryptamine and tryptophol derivatives. Tetrahedron Letters 2023, 123, 154534. doi:10.1016/j.tetlet.2023.154534
• Matviitsuk, A.; Lee Panger, J.; Denmark, S. E. Enantioselective Inter- and Intramolecular Sulfenofunctionalization of Unactivated Cyclic and (Z)-Alkenes. ACS catalysis 2022, 12, 7377–7385. doi:10.1021/acscatal.2c01232
• Cao, R.-F.; Yu, L.; Huo, Y.-X.; Li, Y.; Xue, X.-S.; Chen, Z.-M. Chiral Lewis Base Catalyzed Enantioselective Selenocyclization of 1,1-Disubstituted Alkenes: Asymmetric Synthesis of Selenium-Containing 4H-3,1-Benzoxazines. Organic letters 2022, 24, 4093–4098. doi:10.1021/acs.orglett.2c01731
• Li, E.; Chen, J.; Huang, Y. Enantioselective Seleno‐Michael Addition Reactions Catalyzed by a Chiral Bifunctional N‐Heterocyclic Carbene with Noncovalent Activation. Angewandte Chemie 2022, 134. doi:10.1002/ange.202202040
• Li, E.; Chen, J.; Huang, Y. Enantioselective Seleno-Michael Addition Reactions Catalyzed by a Chiral Bifunctional N-Heterocyclic Carbene with Noncovalent Activation. Angewandte Chemie (International ed. in English) 2022, 61, e202202040. doi:10.1002/anie.202202040
• Wang, J.-Y.; Zhang, S.; Yu, X.-Y.; Wang, Y.-H.; Wan, H.-L.; Zhang, S.; Tan, W.; Shi, F. Organocatalytic asymmetric synthesis of bioactive hexahydropyrrolo[2,3-b]indole-containing tetrasubstituted allenes bearing multiple chiral elements. Tetrahedron Chem 2022, 1, 100007. doi:10.1016/j.tchem.2022.100007
• Hashimoto, T. Olefin Difunctionalization With Two Different Atoms; 1,2-Aaminofunctionalization 1,2-Oxyfunctionalization With Non-halogen Function But B, S, Se. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering; Elsevier, 2022. doi:10.1016/b978-0-32-390644-9.00008-1
• Šmit, B.; Stanić, P. B.; Janković, N. Selenocyclization by Formation of Carbon-nitrogen Bonds. Current organic synthesis 2022, 19, 293–316. doi:10.2174/1570179418666210917152537
• Brydon, S. C.; White, J. M. Comprehensive Heterocyclic Chemistry IV - Three-Membered Rings With One Selenium or Tellurium Atom. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 436–463. doi:10.1016/b978-0-12-409547-2.14760-2
• Lu, Z.-y.; Lan, W.-q.; Liu, F.-y.; Wang, J.-y.; Zhang, X.-M.; Liao, L.-h. Enantioselective synthesis of C3 substituted benzofuroindolines via catalytic asymmetric [3 + 2] cyclization of 3-substituted indoles with p-benzoquinones. Tetrahedron Letters 2021, 76, 153233. doi:10.1016/j.tetlet.2021.153233
• Mei, G.-J.; Koay, W. L.; Tan, C. X. A.; Lu, Y. Catalytic asymmetric preparation of pyrroloindolines: strategies and applications to total synthesis. Chemical Society reviews 2021, 50, 5985–6012. doi:10.1039/d0cs00530d
• Sonawane, A. D.; Koketsu, M. Organocatalysed Synthesis of Selenium Containing Scaffolds. Current Organocatalysis 2021, 8, 5–26. doi:10.2174/2213337207999200414143605
• Lu, Z.-y.; Hu, J.-t.; Lan, W.-q.; Mo, X.-q.; Zhou, S.; Tang, Y.-f.; Yuan, W.-C.; Zhang, X.-M.; Liao, L.-h. Enantioselective synthesis of hetero-triarylmethanes by chiral phosphoric acid-catalyzed 1,4-addition of 3-substituted indoles with azadienes. Tetrahedron Letters 2021, 67, 152862. doi:10.1016/j.tetlet.2021.152862
• Sheng, F.-T.; Wang, J.-Y.; Wei, T.; Zhang, Y.-C.; Shi, F. Progresses in organocatalytic asymmetric dearomatization reactions of indole derivatives. Organic Chemistry Frontiers 2020, 7, 3967–3998. doi:10.1039/d0qo01124j
• Zhang, Y.; Wu, X.-Y.; Han, J.; Wong, H. N. C. Chiral iminophosphorane catalyzed asymmetric phenylselenylation of 3-substituted oxindoles. Tetrahedron Letters 2020, 61, 151559. doi:10.1016/j.tetlet.2019.151559
• Sonawane, A. D.; Koketsu, M. Recent Advances on C-Se Bond-forming Reactions at Low and Room Temperature. Current Organic Chemistry 2020, 23, 3206–3225. doi:10.2174/1385272823666191209111934
• Xia, Z.-L.; Xu-Xu, Q.-F.; Zheng, C.; You, S.-L. Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions. Chemical Society reviews 2020, 49, 286–300. doi:10.1039/c8cs00436f
• Ramesh, B.; Kumar, G. R.; Yarlagadda, S.; Sridhar, B.; Reddy, B. V. S. BINOL-phosphoric acid catalyzed asymmetric Mannich addition of β-ketoesters to indolenines generated in situ by DDQ. Tetrahedron 2019, 75, 130620. doi:10.1016/j.tet.2019.130620
• Cheng, Y.-Z.; Zhao, Q.-R.; Zhang, X.; You, S.-L. Asymmetric Dearomatization of Indole Derivatives with N‐Hydroxycarbamates Enabled by Photoredox Catalysis. Angewandte Chemie (International ed. in English) 2019, 58, 18069–18074. doi:10.1002/anie.201911144

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