Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

Scholarly Works

• Torán, R.; Portillo, E.; Sanz-Marco, A.; Vila, C.; Blay, G. Enantioselective construction of quaternary stereocenters via organocatalytic arylation of isoxazolin-5-ones with o-quinone diimides. Organic Chemistry Frontiers 2023, 10, 6081–6086. doi:10.1039/d3qo01600e
• Chen, Y.; Li, G.-X.; Peng, A.-Q.; Tang, Y.; Wang, L. Rapid Construction of Enantioenriched Benzofurochromanes by SaBOX/Copper(II) Catalyzed Enantioselective [3 + 2] Annulation of γ-Chromenes with Quinones. Organic letters 2022, 24, 5525–5529. doi:10.1021/acs.orglett.2c01933
• Hao, Y.-J.; Hu, X.-S.; Zhou, Y.; Zhou, J.; Yu, J.-S. Catalytic Enantioselective α-Arylation of Carbonyl Enolates and Related Compounds. ACS Catalysis 2019, 10, 955–993. doi:10.1021/acscatal.9b04480
• Qiao, L.; Duan, Z.; Wu, X.-N.; Li, D.; Gu, Q.; Liu, Y.-K. Organocatalytic Diversity-Oriented Asymmetric Synthesis of Structurally and Stereochemically Complex Heterocycles. Organic letters 2018, 20, 1630–1633. doi:10.1021/acs.orglett.8b00377
• Zhang, X.; Chen, Y.-H.; Tan, B. Organocatalytic enantioselective transformations involving quinone derivatives as reaction partners. Tetrahedron Letters 2018, 59, 473–486. doi:10.1016/j.tetlet.2017.12.055
• Dalpozzo, R. Recent Catalytic Asymmetric Syntheses of 3,3-Disubstituted Indolin-2-ones and 2,2-Disubstituted Indolin-3-ones. Advanced Synthesis & Catalysis 2017, 359, 1772–1810. doi:10.1002/adsc.201700361
• Liu, Y.; Li, J.; Ye, X.; Zhao, X.; Jiang, Z. Organocatalytic asymmetric formal arylation of benzofuran-2(3H)-ones with cooperative visible light photocatalysis. Chemical communications (Cambridge, England) 2016, 52, 13955–13958. doi:10.1039/c6cc07105h
• Li, J.; Qiu, S.; Ye, X.; Zhu, B.; Liu, H.; Jiang, Z. Dipeptide-Based Chiral Tertiary Amine-Catalyzed Asymmetric Conjugate Addition Reactions of 5H-Thiazol/Oxazol-4-Ones. The Journal of organic chemistry 2016, 81, 11916–11923. doi:10.1021/acs.joc.6b02384
• Um, S.; Bach, D.-H.; Shin, B.; Ahn, C.-H.; Kim, S.-H.; Bang, H.-S.; Oh, K.-B.; Lee, S. K.; Shin, J.; Oh, D.-C. Naphthoquinone-Oxindole Alkaloids, Coprisidins A and B, from a Gut-Associated Bacterium in the Dung Beetle, Copris tripartitus. Organic letters 2016, 18, 5792–5795. doi:10.1021/acs.orglett.6b02555
• Li, N.-K.; Kong, L.-P.; Qi, Z.-H.; Yin, S.-J.; Zhang, J.-Q.; Wu, B.; Wang, X.-W. Friedel–Crafts Reaction of Indoles with Isatin‐Derived β,γ‐Unsaturated α‐Keto Esters Using a BINOL‐Derived Bisoxazoline (BOX)/Copper(II) Complex as Catalyst. Advanced Synthesis & Catalysis 2016, 358, 3100–3112. doi:10.1002/adsc.201600272
• Hosamani, B.; Ribeiro, M. F.; da Silva Júnior, E. N.; Namboothiri, I. N. N. Catalytic asymmetric reactions and synthesis of quinones. Organic & biomolecular chemistry 2016, 14, 6913–6931. doi:10.1039/c6ob01119e
• He, Y.; Bao, X.; Qu, J.; Wang, B. Asymmetric tandem Michael addition/oxidation of pyrazolones with p-benzoquinone catalyzed by cinchona alkaloids. Tetrahedron: Asymmetry 2015, 26, 1382–1387. doi:10.1016/j.tetasy.2015.10.006
• Chen, L.; You, Y.; Zhang, M.-L.; Zhao, J.-Q.; Zuo, J.; Zhang, X.-M.; Yuan, W.-C.; Xu, X.-Y. Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3′-disubstituted oxindoles with chiral squaramides. Organic & biomolecular chemistry 2015, 13, 4413–4417. doi:10.1039/c5ob00317b
• Liao, L.; Shu, C.; Zhang, M.; Liao, Y.; Hu, X.; Zhang, Y.; Wu, Z.; Yuan, W.; Zhang, X. Highly Enantioselective [3+2] Coupling of Indoles with Quinone Monoimines Promoted by a Chiral Phosphoric Acid. Angewandte Chemie 2014, 126, 10639–10643. doi:10.1002/ange.201405689
• Liao, L.-H.; Shu, C.; Zhang, M.; Liao, Y.; Hu, X.-Y.; Zhang, Y.; Wu, Z.-J.; Yuan, W.-C.; Zhang, X.-M. Highly Enantioselective [3+2] Coupling of Indoles with Quinone Monoimines Promoted by a Chiral Phosphoric Acid. Angewandte Chemie (International ed. in English) 2014, 53, 10471–10475. doi:10.1002/anie.201405689
• Chen, L.; Yin, X.-P.; Wang, C.-H.; Zhou, J. Catalytic functionalization of tertiary alcohols to fully substituted carbon centres. Organic & biomolecular chemistry 2014, 12, 6033–6048. doi:10.1039/c4ob00718b
• Wang, Y.-H.; Liu, Y.-L.; Cao, Z.-Y.; Zhou, J. An Organocatalytic Addition of Nitromethane to Activated Ketimines. Asian Journal of Organic Chemistry 2014, 3, 429–432. doi:10.1002/ajoc.201300289
• Zhang, Y.; Hu, X.-Y.; Li, S.-S.; Liao, Y.; Yuan, W.-C.; Zhang, X.-M. Organocatalytic enantioselective tandem Michael addition-oxidation of 3-substituted oxindoles with 1,4-benzoquinone. Tetrahedron 2014, 70, 2020–2026. doi:10.1016/j.tet.2014.01.067
• Gao, J.; Chen, J.-R.; Duan, S.-W.; Li, T.-R.; Lu, L.-Q.; Xiao, W.-J. Organocatalytic Asymmetric Conjugate Addition of 2-Oxindole-3-Carboxylate Esters to 2-Phthalimido Acrylates: Efficient Synthesis of Cγ-tetrasubstituted α-Amino Acid Derivatives. Asian Journal of Organic Chemistry 2014, 3, 530–535. doi:10.1002/ajoc.201300292
• Zielińska-Błajet, M.; Skarżewski, J. Stereoselective Dithiophosphorylation of Cinchona Alkaloids: Easy Approach to Prospective Chiral Ligands and Organocatalysts. Phosphorus, Sulfur, and Silicon and the Related Elements 2013, 188, 1811–1818. doi:10.1080/10426507.2013.788000

Explore citations to this article at