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Catalytic Asymmetric [4+2] Cyclization of Hydroxyphenyl Indolinone with Azlactone to Construct Spirooxindole δ-Lactone

Xuerui Wang

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao, Shandong, 266003 China

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Weiwu Ren,

Corresponding Author

Weiwu Ren

[email protected]

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao, Shandong, 266003 China

Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao, Shandong, 266237 China

E-mail: [email protected]Search for more papers by this author

Xuerui Wang,

Xuerui Wang

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao, Shandong, 266003 China

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Weiwu Ren,

Corresponding Author

Weiwu Ren

[email protected]

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao, Shandong, 266003 China

Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao, Shandong, 266237 China

E-mail: [email protected]Search for more papers by this author

First published: 10 September 2024

https://doi.org/10.1002/cjoc.202400777

Citations: 3

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Comprehensive Summary

An efficient asymmetric [4+2] cyclization of hydroxyphenyl indolinone with azlactone for the synthesis of spirooxindole δ-lactone has been developed, which realized the first asymmetric reaction of hydroxyphenyl indolinone. A series of intricate structures with congested vicinal quaternary chiral centers were provided in good yields with excellent enantioselectivities via the in situ generated o-QM from hydroxyphenyl indolinone.

Supporting Information

References

1(a) Chafeev, M.; Chowdhury, S.; Fraser, R.; Fu, J.; Kamboj, R.; Hou, D.; Liu, S.; Bagherzadeh, M. S.; Sviridov, S.; Sun, S.; Sun, J.; Chakka, N.; Hsieh, T.; Raina, V. WO2006110917-A2, 2006;
Google Scholar
(b) Chafeev, M.; Chowdhury, S.; Fraser, R.; Fu, J.; Kamboj, R.; Hou, D.; Liu, S.; Seid Bagherzadeh, M.; Sviridov, S.; Sun, S.; Sun, J.; Chakka, N.; Hsieh, T.; Raina, V. WO2008060789-A2, 2008;
Google Scholar
(c) Padiya, K. J.; Nair, P. S.; Pal, R. R.; Chaure, G. S.; Gudade, G. B.; Parkale, S. S.; Manojkumar, V. L.; Swapnil, R. B.; Smita, A. B. Spirocyclic Compounds as Voltage-gated Sodium Channel Modulators. WO2012049555-A1, 2012.
Google Scholar
2 Wen, Y.-H.; Yang, F.; Li, S.; Yao, X.; Song, J.; Gong, L.-Z. Diastereodivergent Desymmetric Annulation to Access Spirooxindoles: Chemical Probes for Mitosis. J. Am. Chem. Soc. 2023, 145, 4199–4207.
10.1021/jacs.2c12648
CAS Google Scholar
3 Ma, S.-S.; Mei, W.-L.; Guo, Z.-K.; Liu, S.-B.; Zhao, Y.-X.; Yang, D.-L.; Zeng, Y.-B.; Jiang, B.; Dai, H.-F. Two New Types of Bisindole Alkaloid from Trigonostemon Lutescens. Org. Lett. 2013, 15, 1492–1495.
10.1021/ol4002619
CAS PubMed Web of Science® Google Scholar
4 Cai, X.-H.; Tan, Q.-G.; Liu, Y.-P.; Feng, T.; Du, Z.-Z.; Li, W.-Q.; Luo, X.-D. A Cage-Monoterpene Indole Alkaloid from Alstonia Scholaris. Org. Lett. 2008, 10, 577–580.
10.1021/ol702682h
CAS PubMed Web of Science® Google Scholar
5(a) Zhang, Z.-J.; Zhang, L.; Geng, R.-L.; Song, J.; Chen, X.-H.; Gong, L.-Z. N-Heterocyclic Carbene/Copper Cooperative Catalysis for the Asymmetric Synthesis of Spirooxindoles. Angew. Chem. Int. Ed. 2019, 58, 12190–12194;
10.1002/anie.201907188
CAS PubMed Web of Science® Google Scholar
(b) Fan, T.; Song, J.; Gong, L.-Z. Asymmetric Redox Allylic Alkylation to Access 3,3’-Disubstituted Oxindoles Enabled by Ni/NHC Cooperative Catalysis. Angew. Chem. Int. Ed. 2022, 61, e202201678;
10.1002/anie.202201678
CAS PubMed Web of Science® Google Scholar
(c) Wen, Y.-H.; Yang, F.; Li, S.; Yao, X.; Song, J.; Gong, L.-Z. Diastereodivergent Desymmetric Annulation to Access Spirooxindoles: Chemical Probes for Mitosis. J. Am. Chem. Soc. 2023, 145, 4199–4207.
10.1021/jacs.2c12648
CAS Google Scholar
6 Yang, X.; Sun, J.; Huang, X.; Jin, Z. Asymmetric Synthesis of Structurally Sophisticated Spirocyclic Pyrano-[2,3-c]pyrazole Derivatives Bearing a Chiral Quaternary Carbon Center. Org. Lett. 2022, 24, 5474–5479.
10.1021/acs.orglett.2c02211
CAS PubMed Google Scholar
7 Hu, H.; Teng, F.; Liu, J.; Hu, W.; Luo, S.; Zhu, Q. Enantioselective Synthesis of 2-Oxindole Spirofused Lactones and Lactams by Heck/Carbonylative Cyclization Sequences: Method Development and Applications. Angew. Chem. Int. Ed. 2019, 58, 9225–9229.
10.1002/anie.201904838
CAS PubMed Web of Science® Google Scholar
8 Zhao, S.; Lin, J.-B.; Zhao, Y.-Y.; Liang, Y.-M.; Xu, P.-F. Hydrogen-Bond- Directed Formal [5+1] Annulations of Oxindoles with Ester-linked Bisenones: Facile Access to Chiral Spirooxindole δ-Lactones. Org. Lett. 2014, 16, 1802–1805.
10.1021/ol500547e
CAS PubMed Web of Science® Google Scholar
9(a) Shi, H.; Wang, L.; Li, S.-S.; Liu, Y.; Xu, L. Divergent Syntheses of Spirooxindoles from Oxindole-embedded Four-membered Synthon via Cycloaddition Reactions. Org. Chem. Front. 2020, 7, 747–755;
10.1039/D0QO00038H
CAS Web of Science® Google Scholar
(b) Hu, F.; Wang, L.; Wang, P.; Ding, Z.; Chen, Y.; Xu, L.; Liu, X.-L.; Li, S.-S. Switchable Construction of Oxa-heterocycles with Diverse Ring Sizes via Chemoselective Cyclization Controlled by Dibrominated Compounds. Org. Chem. Front. 2022, 9, 6187–6193.
10.1039/D2QO01273A
CAS Google Scholar
10(a) Kim, H.; Kim, S.-G. [4+2] Annulation of δ-Hydroxy/ δ-Sulfonamido-α,β-unsaturated Ketones with Azlactones for Diastereoselective Synthesis of Highly Substituted 3-Amino-δ-lactones and 3-Amino-δ-lactams. J. Org. Chem. 2023, 88, 3830–3844;
10.1021/acs.joc.3c00065
PubMed Google Scholar
(b) Wang, L.; Liu, M.; Lu, M.; Wang, B.; Han, Q.; Jin, J.; Yu, S.; Wu, Y.; Guo, H. Palladium-catalyzed [4+2] Cycloaddition of Amido-tethered Allylic Carbonates with Oxazol-5-(4H)-ones: Synthesis of Piperidine-2,6-dione Derivatives. Org. Chem. Front. 2023, 10, 813–818;
10.1039/D2QO01783K
CAS Google Scholar
(c) Castro, P. P.; Carpanez, A. G.; Amarante, G. W. Azlactone Reaction Developments. Chem. Eur. J. 2016, 22, 10294–10318.
Google Scholar

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Volume42, Issue24

15 December 2024

Pages 3362-3366

Catalytic Asymmetric [4+2] Cyclization of Hydroxyphenyl Indolinone with Azlactone to Construct Spirooxindole δ-Lactone

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Catalytic Asymmetric [4+2] Cyclization of Hydroxyphenyl Indolinone with Azlactone to Construct Spirooxindole δ-Lactone

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