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The Direct Amino Acid-Catalyzed Asymmetric Incorporation of Molecular Oxygen to Organic Compounds
Abstract
We have disclosed the direct catalytic incorporation of 1O2 to aldehydes. The unprecedented amino acid-catalyzed asymmetric alpha-oxidation of aldehydes with molecular oxygen or air proceeded with high chemoselectivity and was a direct entry for the synthesis of both enantiomers of terminal diols. The results demonstrated that simple amino acids accomplished catalytic asymmetric oxidations with molecular oxygen or air, which has previously been considered to be in the domain of enzymes and chiral transition-metal complexes. The efficiency of the catalytic process may warrant the existence of an ancient pathway for the synthesis of hydroxylated organic compounds.
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Cites
Free Radicals in Biology and Medicine
Halliwell, B., & Gutteridge, J. M. C. (2015) · doi:10.1093/acprof:oso/9780198717478.001.0001 · Cited by 8,990
Physical Mechanisms of Generation and Deactivation of Singlet Oxygen
Schweitzer, C., & Schmidt, R. (2003) · Chemical Reviews · doi:10.1021/cr010371d · Cited by 2,123
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Dual Catalysis Strategies in Photochemical Synthesis
Skubi, K. L., Blum, T. R., & Yoon, T. P. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00018 · Cited by 2,686
Photochemical Reactions as Key Steps in Organic Synthesis
Hoffmann, N. (2008) · Chemical Reviews · doi:10.1021/cr0680336 · Cited by 1,445
Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry
Melchiorre, P., Marigo, M., Carlone, A., & Bartoli, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705523 · Cited by 1,256
Visible‐Light‐Induced Organic Photochemical Reactions through Energy‐Transfer Pathways
Zhou, Q., Zou, Y., Lu, L., & Xiao, W. (2019) · Angewandte Chemie International Edition · doi:10.1002/anie.201803102 · Cited by 1,156
Franzén, J., Marigo, M., Fielenbach, D., Wabnitz, T. C., Kjærsgaard, A., & Jørgensen, K. A. (2005) · Journal of the American Chemical Society · doi:10.1021/ja056120u · Cited by 640
Metadata
- Authors
- Córdova, A., Sundén, H., Engqvist, M., Ibrahem, I., & Casas, J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-07-01
- Volume
- 126
- Issue
- 29
- Pages
- 8914-8915
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2158222185
- Cited by
- 220
- References
- 2
- FWCI
- 15.04
- Type
- journal article
- Language
- en
- Open access
- closed
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- Córdova, A., Sundén, H., Engqvist, M., Ibrahem, I., & Casas, J. (2004). The Direct Amino Acid-Catalyzed Asymmetric Incorporation of Molecular Oxygen to Organic Compounds. Journal of the American Chemical Society. https://doi.org/10.1021/ja047930t
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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.