Categories: C-O Bond Formation, Synthesis of cyclic ethers >
Synthesis of epoxides
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Recent Literature
The asymmetric addition of chiral sulfonium ylides to aldehydes is promoted
by 2,5-dimethylthiolanes with a locked conformation. This user-friendly
organocatalytic process proved to be efficient with 20-10% of sulfide in 1
or 2 days of reaction.
M. Davoust, J.-F. Briere, P.-A. Jaffres, P. Metzner, J. Org. Chem., 2005,
70, 4166-4169.
A camphor-derived amide-stabilized ylide reacts with aldehydes at -50°C in
ethanol to give glycidic amides in one step with up to 99% ee and complete
diastereoselectivity. Further transformations of epoxyamides were
investigated.
V. K. Aggarwal, G. Hynd, W. Picoul, J.-L. Vasse, J. Am. Chem. Soc.,
2002,
124, 9964-9965.
The first Corey-Chaykovsky epoxidation and cyclopropanation using trimethyl
sulfonium iodide/trimethyl sulfoxonium iodide and KOH as base in the recyclable
ionic liquid, (bmim)PF6 are described.
S. Chandrasekhar, Ch. Narasihmulu, V. Jagadeshwar, K. Venkatram Reddy,
Tetrahedron Lett., 2003,
44, 3629-3630.
A highly stereoselective synthesis of aromatic α,β-unsaturated amides was
achieved by treatment of aromatic α,β-epoxyamides with samarium diiodide.
α,β-epoxyamides are easily prepared by the reaction of enolates derived from
α-chloroamides with carbonyl compounds at -78°C.
J. M. Concellón, E. Bardales, J. Org. Chem., 2003,
5, 9492-9295.
J. M. Concellón, E. Bardales, J. Org. Chem., 2003,
5, 9492-9295.
