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Iridium-Catalyzed Enantioselective Allylic Substitution with Aqueous Solutions of Nucleophiles.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2019 Aug 07; Vol. 141 (31), pp. 12212-12218. Date of Electronic Publication: 2019 Jul 26. - Publication Year :
- 2019
-
Abstract
- The iridium-catalyzed asymmetric allylic substitution under biphasic conditions is reported. This approach allows the use of various unstable and/or volatile nucleophiles including hydrazines, methylamine, t -butyl hydroperoxide, N -hydroxylamine, α-chloroacetaldehyde and glutaraldehyde. This transformation provides rapid access to a broad range of products from simple starting materials in good yields and up to >99% ee and 20:1 d.r. Additionally, these products can be elaborated efficiently into a diverse set of cyclic and acyclic compounds, bearing up to four stereocenters.
Details
- Language :
- English
- ISSN :
- 1520-5126
- Volume :
- 141
- Issue :
- 31
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 31318204
- Full Text :
- https://doi.org/10.1021/jacs.9b05830