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Oxidative Cyclization of 1,5-Dienes with Hydrogen Peroxide Catalyzed by an Osmium(III) Complex: Synthesis of cis-Tetrahydrofurans.
- Source :
-
Organic letters [Org Lett] 2016 Mar 18; Vol. 18 (6), pp. 1246-9. Date of Electronic Publication: 2016 Mar 07. - Publication Year :
- 2016
-
Abstract
- Stereoselective oxidative cyclization of 1,5-dienes with hydrogen peroxide catalyzed by [Os(III)(OH)(H2O)(L-N4Me2)](PF6)2 (1: L-N4Me2 = N,N'-dimethyl-2,11-diaza-[3,3](2,6)pyridinophane) is explored. 1,5-Dienes involving geraniol derivatives are converted to the corresponding tetrahydrofurans in modest to high yields. The products exclusively have the cis-conformation with respect to the substituents at the 2- and 5-positions of the tetrahydrofuran ring. The products also have a syn-conformation with respect to the furan oxygen atom and the hydroxyl groups. Mechanistic studies including a direct reaction of the oxo-hydroxo-osmium(V) complex, 2, with a dihydroxylated geraniol derivative are performed.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 18
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 26950609
- Full Text :
- https://doi.org/10.1021/acs.orglett.6b00064