The DOI matches its Crossref record; 17 of the 17 references it cites were found in a registry or an index.
Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine
Abstract
Oxindoles and their indoline derivatives are common structural motifs found in a wide array of natural and biologically active molecules. Most catalytic methods for the asymmetric syntheses of these compounds rely heavily on the use of transition-metal catalysts. In contrast, alternative catalytic procedures involving organocatalysis are scarce. Herein we disclose a conceptually novel organocatalytic approach to the syntheses of these materials using thiourea-catalyzed asymmetric 1,4-additions of oxindole derivatives to nitroolefins as a key step. These addition reactions create up to two stereogenic centers, one of which is a quaternary center. These reactions are broad in scope with respect to both the oxindole and nitroolefin substrates and provide the desired products in good yields with enantioselectivities of up to 99% and diastereoselectivities of up to >20:1. To demonstrate the utility of this approach, (+)-esermethole was synthesized in good overall yield over 3 steps starting from the 1,4-addition product, thereby providing a formal synthesis of (+)-physostigmine.
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Cites
Small-Molecule H-Bond Donors in Asymmetric Catalysis
Doyle, A. G., & Jacobsen, E. N. (2007) · Chemical Reviews · doi:10.1021/cr068373r · Cited by 2,608
Asymmetric Catalysis by Chiral Hydrogen‐Bond Donors
Taylor, M. S., & Jacobsen, E. N. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200503132 · Cited by 1,906
Marti, C., & Carreira, E. M. (2003) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200300050 · Cited by 1,455
Okino, T., Hoashi, Y., & Takemoto, Y. (2003) · Journal of the American Chemical Society · doi:10.1021/ja036972z · Cited by 1,430
Okino, T., Hoashi, Y., Furukawa, T., Xu, X., & Takemoto, Y. (2005) · Journal of the American Chemical Society · doi:10.1021/ja044370p · Cited by 1,061
Sigman, M. S., & Jacobsen, E. N. (1998) · Journal of the American Chemical Society · doi:10.1021/ja980139y · Cited by 910
Organocatalytic asymmetric conjugate additions
Almaşi, D., Alonso, D. A., & Nájera, C. (2007) · Tetrahedron: Asymmetry · doi:10.1016/j.tetasy.2007.01.023 · Cited by 859
Vachal, P., & Jacobsen, E. N. (2002) · Journal of the American Chemical Society · doi:10.1021/ja027246j · Cited by 577
Wenzel, A. G., & Jacobsen, E. N. (2002) · Journal of the American Chemical Society · doi:10.1021/ja028353g · Cited by 564
Herrera, R. P., Sgarzani, V., Bernardi, L., & Ricci, A. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200500227 · Cited by 465
Cited by
Zhou, F., Liu, Y., & Zhou, J. (2010) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201000161 · Cited by 1,252
Recent advances in organocatalytic methods for the synthesis of disubstituted 2- and 3-indolinones
Dalpozzo, R., Bartoli, G., & Bencivenni, G. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35100e · Cited by 673
Chen, X.-H., Wei, Q., Luo, S.-W., Xiao, H., & Gong, L.-Z. (2009) · Journal of the American Chemical Society · doi:10.1021/ja905302f · Cited by 577
Bencivenni, G., Wu, L., Mazzanti, A., Giannichi, B., Pesciaioli, F., Song, M., Bartoli, G., & Melchiorre, P. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200903192 · Cited by 448
Wang, X., Liu, J., Xu, L., Hao, Z., Wang, L., & Xiao, J. (2015) · RSC Advances · doi:10.1039/c5ra21919a · Cited by 28
Metadata
- Authors
- Bui, T., Syed, S., & Barbas, C. F.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-06-05
- Volume
- 131
- Issue
- 25
- Pages
- 8758-8759
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2086311749
- Cited by
- 351
- References
- 17
- FWCI
- 22.35
- Type
- journal article
- Language
- en
- Open access
- closed
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