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Gold(III) Salen Complex-Catalyzed Synthesis of Propargylamines via a Three-Component Coupling Reaction
Abstract
[reaction: see text] Propargylamines have been synthesized by a gold(III) salen complex-catalyzed three-component coupling reaction of aldehydes, amines, and alkynes in water in excellent yields at 40 degrees C. With chiral prolinol derivatives as the amine component, excellent diastereoselectivities (up to 99:1) have been attained. This coupling reaction has been applied to the synthesis of propargylamine-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. Cytotoxicities with IC(50) values up to 1.1 microM against a human hepatocellular carcinoma cell line (HepG2) were exhibited by these artemisinin derivatives.
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Haynes, R. K., & Vonwiller, S. C. (1997) · Accounts of Chemical Research · doi:10.1021/ar950058w · Cited by 220
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Hashmi, A. S. K., & Hutchings, G. J. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200602454 · Cited by 3,423
Datta, K. K. R., Reddy, B. V. S., Ariga, K., & Vinu, A. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201001699 · Cited by 375
Zeng, T., Chen, W.-W., Cirtiu, C. M., Moores, A., Song, G., & Li, C.-J. (2010) · Green Chemistry · doi:10.1039/b920000b · Cited by 300
Lo, V. K., Liu, Y., Wong, M., & Che, C. (2006) · ChemInform · doi:10.1002/chin.200634049 · Cited by 298
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Metadata
- Authors
- Lo, V. K.-Y., Liu, Y., Wong, M.-K., & Che, C.-M.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-03-17
- Volume
- 8
- Issue
- 8
- Pages
- 1529-1532
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2039884969
- Cited by
- 371
- References
- 1
- FWCI
- 14.76
- Type
- journal article
- Language
- en
- Open access
- closed
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- Lo, V. K.-Y., Liu, Y., Wong, M.-K., & Che, C.-M. (2006). Gold(III) Salen Complex-Catalyzed Synthesis of Propargylamines via a Three-Component Coupling Reaction. Organic Letters. https://doi.org/10.1021/ol0528641
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