The DOI matches its Crossref record.
trans-RuH(η-BH4)(binap)(1,2-diamine): A Catalyst for Asymmetric Hydrogenation of Simple Ketones under Base-Free Conditions
Abstract
Reaction of a chiral RuCl2(diphosphine)(1,2-diamine) complex and NaBH4 forms trans-RuH(eta1-BH4)(diphosphine)(1,2-diamine) quantitatively. The TolBINAP/DPEN Ru complex has been characterized by single crystal X-ray analysis as well as NMR and IR spectra. The new Ru complexes allow for asymmetric hydrogenation of simple ketones in 2-propanol without an additional strong base. Various base-sensitive ketones are convertible to chiral alcohols in a high enantiomeric purity with a substrate/catalyst ratio of up to 100 000 under mild conditions. Configurationally unstable 2-isopropyl- and 2-methoxycyclohexanone can be kinetically resolved with a high enantiomer discrimination. This procedure overcomes the drawback of an earlier method using RuCl2(diphosphine)(diamine) and an alkaline base, which sometimes causes undesired reactions such as ester exchange, epoxy-ring opening, beta-elimination, and polymerization of ketonic substrates.
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Citations
Cited by
Pârvulescu, V. I., & Hardacre, C. (2007) · Chemical Reviews · doi:10.1021/cr050948h · Cited by 2,377
Clapham, S. E., Hadzovic, A., & Morris, R. H. (2004) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2004.04.007 · Cited by 1,316
Chiral Synthesis on Catalysts Immobilized in Microporous and Mesoporous Materials
Li, C. (2004) · Catalysis Reviews · doi:10.1081/cr-200036734 · Cited by 357
Noyori, R., Kitamura, M., & Ohkuma, T. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0307928100 · Cited by 277
Self-citationZahrt, A. F., Athavale, S. V., & Denmark, S. E. (2020) · Chemical Reviews · doi:10.1021/acs.chemrev.9b00425 · Cited by 212
Metadata
- Authors
- Ohkuma, T., Koizumi, M., Muñiz, K., Hilt, G., Kabuto, C., & Noyori, R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-05-15
- Volume
- 124
- Issue
- 23
- Pages
- 6508-6509
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1970765732
- Cited by
- 308
- References
- 0
- FWCI
- 14.24
- Type
- journal article
- Language
- en
- Open access
- closed
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