The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity
Abstract
The privileged spiro[pyrrolidin-3,3'-oxindole] derivatives exhibit important biological activities. An enantioselective organocatalytic approach to the rapid synthesis of spiro[pyrrolidin-3,3'-oxindole] derivatives with high enantiopurity and structural diversity is described. The asymmetric catalytic three-component 1,3-dipolar cycloaddition of a broad range of methyleneindolinones with aldehydes and amino esters in the presence of chiral phosphoric acid provides spirooxindole derivatives in high yield with unusual regiochemistry and excellent stereoselectivities (up to 98% ee) under mild conditions. The straightforward construction of spirooxindole skeletons with high stereo- and regioselectivity suggests a new avenue to medicinal chemistry and diversity-oriented synthesis. Theoretical calculations disclosed that both the azomethine ylide and the methyleneindolinone are hydrogen-bonded with the phosphoric acid, which accounted for the high enantio- and regioselectivity and indicated that the unusual regioselectivity results from the stabilization stemming from the favorable pi-pi stacking interaction between the oxo-indole ring and the conjugated esters.
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Ding, K., Lu, Y., Nikolovska-Coleska, Z., Wang, G., Qiu, S., Shangary, S., Gao, W., Qin, D., Stuckey, J., Krajewski, K., et al. (2006) · Journal of Medicinal Chemistry · doi:10.1021/jm051122a · Cited by 702
Shangary, S., Qin, D., McEachern, D., Liu, M., Miller, R. S., Qiu, S., Nikolovska-Coleska, Z., Ding, K., Wang, G., Chen, J., et al. (2008) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0708917105 · Cited by 660
Structure-based design of potent non-peptide MDM2 inhibitors
Ding, K., Lu, Y., Nikolovska-Coleska, Z., Qiu, S., Ding, Y., Gao, W., Stuckey, J., Krajewski, K., Roller, P. P., Tomita, Y., et al. (2005) · Journal of the American Chemical Society · doi:10.1021/ja051147z · Cited by 657
Cited by
Parmar, D., Sugiono, E., Raja, S., & Rueping, M. (2014) · Chemical Reviews · doi:10.1021/cr5001496 · Cited by 2,118
Zhou, F., Liu, Y., & Zhou, J. (2010) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201000161 · Cited by 1,252
Recent Advances of Catalytic Asymmetric 1,3-Dipolar Cycloadditions
Hashimoto, T., & Maruoka, K. (2015) · Chemical Reviews · doi:10.1021/cr5007182 · Cited by 1,018
Liu, Y., Nappi, M., Arceo, E., Vera, S., & Melchiorre, P. (2011) · Journal of the American Chemical Society · doi:10.1021/ja206517s · Cited by 398
Catalytic Enantioselective Construction of Spiro Quaternary Carbon Stereocenters
Xu, P.-W., Yu, J.-S., Chen, C., Cao, Z.-Y., Zhou, F., & Zhou, J. (2019) · ACS Catalysis · doi:10.1021/acscatal.8b03694 · Cited by 325
Diastereomeric spirooxindoles as highly potent and efficacious MDM2 inhibitors
Zhao, Y., Liu, L., Sun, W., Lu, J., McEachern, D., Li, X., Yu, S., Bernard, D., Ochsenbein, P., Ferey, V., et al. (2013) · Journal of the American Chemical Society · doi:10.1021/ja3125417 · Cited by 234
Metadata
- Authors
- Chen, X.-H., Wei, Q., Luo, S.-W., Xiao, H., & Gong, L.-Z.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-09-09
- Volume
- 131
- Issue
- 38
- Pages
- 13819-13825
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2087197572
- Cited by
- 577
- References
- 3
- FWCI
- 26.66
- Type
- journal article
- Language
- en
- Open access
- closed
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