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Mo-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation of 3-Aryloxindoles
Open accessAbstract
A highly regio-, diastereo-, and enantioselective allylic alkylation reaction mediated by a chiral molybdenum catalyst has been developed as a novel entry into synthetically versatile 3-alkyl-3-aryloxindoles. Extremely bulky nucleophiles were employed to form a quaternary center and an adjacent tertiary center asymmetrically concurrently. The regio- and diastereoselectivity of the reaction is dependent upon the steric and electronic nature of the nucleophiles to an unusual degree. A reaction mechanism based on the bonding modes of molybdenum enolate complexes was discussed.
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Citations
Cited by
Zhou, F., Liu, Y., & Zhou, J. (2010) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.201000161 · Cited by 1,252
Bui, T., Syed, S., & Barbas, C. F. (2009) · Journal of the American Chemical Society · doi:10.1021/ja903520c · Cited by 351
Wang, X., Liu, J., Xu, L., Hao, Z., Wang, L., & Xiao, J. (2015) · RSC Advances · doi:10.1039/c5ra21919a · Cited by 28
Metadata
- Authors
- Trost, B. M., & Zhang, Y.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-11-07
- Volume
- 129
- Issue
- 47
- Pages
- 14548-14549
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2036407962
- Cited by
- 196
- References
- 0
- FWCI
- 9.65
- Type
- journal article
- Language
- en
- Open access
- green
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- Trost, B. M., & Zhang, Y. (2007). Mo-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation of 3-Aryloxindoles. Journal of the American Chemical Society. https://doi.org/10.1021/ja0755717
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
