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Catalytic Asymmetric Aminohydroxylation (AA) of Olefins
Abstract
The stereospecific cis addition of “TsN” and H2O yields α-hydroxy-N-tosylamines (see below). This osmium-catalyzed process, which depends on Chloramine-T as the nitrenoid source, is rendered asymmetric in the presence of cinchona alkaloid ligands. The selectivities for reactions of the six olefins studied range from 33% ee (cis-stilbene) to 81% ee (trans-methylcinnamate). The active agent is presumably the compound Os(O)3NTs shown in square brackets. (DHQ)2-PHAL = bis(dihydro-quininyl)phthalazine (see preceding communication).
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Citations
Cited by
Stereoselective Organic Reactions in Water
Lindström, U. M. (2002) · Chemical Reviews · doi:10.1021/cr010122p · Cited by 1,642
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Rossiter, S. E., Fletcher, M. H., & Wuest, W. M. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00283 · Cited by 622
Metadata
- Authors
- Li, G., Chang, H., & Sharpless, K. B.
- Venue
- Angewandte Chemie International Edition in English
- Publisher
- Wiley
- Published
- 1996-03
- Volume
- 35
- Issue
- 4
- Pages
- 451-454
- ISSN
- 0570-0833 (ISSN-L)
- OpenAlex
- W2162354594
- Cited by
- 696
- References
- 0
- FWCI
- 31.71
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Catalytic Asymmetric Aminohydroxylation (AA) of Olefins. https://app.cochat.ai/papers/10.1002/anie.199604511
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- Li, G., Chang, H., & Sharpless, K. B. (1996). Catalytic Asymmetric Aminohydroxylation (AA) of Olefins. Angewandte Chemie International Edition in English. https://doi.org/10.1002/anie.199604511
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