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Enantioselective formal α-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction-Julia-Kocienski olefination sequence.
- Source :
-
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2014 Apr 04; Vol. 50 (26), pp. 3491-3. Date of Electronic Publication: 2014 Feb 20. - Publication Year :
- 2014
-
Abstract
- A two-step sequence for the asymmetric formal α-allylation of nitroalkanes is disclosed. This new methodology relies on the development of a highly diastereo- and enantioselective conjugate addition of nitroalkanes to vinylic 2-phenyl-1H-tetrazol-5-ylsulfones using chiral triaminoiminophosphorane as a requisite base catalyst and subsequent Julia-Kocienski olefination under kinetic conditions.
- Subjects :
- Catalysis
Stereoisomerism
Alkanes chemistry
Imines chemistry
Phosphoranes chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1364-548X
- Volume :
- 50
- Issue :
- 26
- Database :
- MEDLINE
- Journal :
- Chemical communications (Cambridge, England)
- Publication Type :
- Academic Journal
- Accession number :
- 24553728
- Full Text :
- https://doi.org/10.1039/c3cc49477b