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DOI: 10.1055/a-2061-0855
Synthesis of Functionalized Spirooxindole Polycycles: Use of Cyclic 1,3-Diones as Reactants or as Condition-Tuning Molecules
This study was supported by the Okinawa Institute of Science and Technology Graduate University.
Abstract
This account describes the strategies for the synthesis of functionalized spirooxindole polycycles, including enantiomerically enriched forms, that we have developed and reported. The syntheses of these complex molecules were accomplished in a few steps starting from relatively simple oxindole derivatives and other reactants. Organocatalytic reactions involved in kinetic resolution or in dynamic kinetic transformation led to the formation of products with high diastereo- and/or enantioselectivities. Cyclic 1,3-diones, such as 1,3-cyclohexanedione, were used as reactants to provide two reaction sites for the construction of polycyclic ring systems. To tune the reaction conditions, 2-methyl-1,3-cyclohexanedione was employed. The developed methods enabled the synthesis of complex functionalized spirooxindole polycycles bearing up to seven stereogenic centers, and will be useful for the synthesis of potentially bioactive molecules.
1 Introduction
2 Formal (4+1) Cycloaddition and Enantioselective Michael/Henry Cascade Reactions
3 Dynamic Stereoselective Aldol/Oxacyclization Cascade Reactions
4 Dynamic Kinetic Asymmetric Transformation: Diastereo- and Enantioconvergent Michael/Henry Reactions
5 Dimerization Reactions
6 Conclusion
Key words
asymmetric catalysis - annulation - cycloadditions - enantioselectivity - Michael addition - organocatalysisPublication History
Received: 20 February 2023
Accepted after revision: 22 March 2023
Accepted Manuscript online:
23 March 2023
Article published online:
26 April 2023
© 2023. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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References
- 1a Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
- 1b Ye N, Chen H, Wold EA, Shi P.-Y, Zhou J. ACS Infect. Dis. 2016; 2: 382
- 1c Han B, He X.-H, Liu Y.-Q, He G, Peng C, Li J.-L. Chem. Soc. Rev. 2021; 50: 1522
- 1d Cheng D, Ishihara Y, Tan B, Barbas CF. III. ACS Catal. 2014; 4: 743
- 1e He Z.-L, Chen P, Chen Z.-C, Du W, Chen Y.-C. Org. Lett. 2022; 24: 100
- 1f Zhou F, Zhou L, Jing P, Sun M, Deng G, Liang Y, Yang Y. Org. Lett. 2022; 24: 1400
- 1g Wang D, Sun J, Han Y, Sun Q, Yan C.-G. Org. Lett. 2022; 24: 7790
- 1h You Z.-H, Liu Y.-K. Org. Lett. 2022; 24: 6288
- 1i Wen Y.-H, Yang F, Li S, Yao X, Song J, Gong L.-Z. J. Am. Chem. Soc. 2023; 145: 4199
- 2 Huang J.-R, Sohail M, Taniguchi T, Monde K, Tanaka F. Angew. Chem. Int. Ed. 2017; 56: 5853
- 3 Sohail M, Tanaka F. Commun. Chem. 2019; 2: 73
- 4 Sohail M, Tanaka F. Angew. Chem. Int. Ed. 2021; 60: 21256
- 5 Sohail M, Tanaka F. Chem. Eur. J. 2020; 26: 222
- 6 Pasha M, Sohail M, Tanaka F. Heterocycles 2020; 101: 339