Categories: C-O Bond Formation, Synthesis of cyclic ethers >
Synthesis of epoxides
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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.
Catalytic (Asymmetric) Methylene Transfer to Aldehydes
A. Piccinini, S. A. Kavanagh, P. B. Connon, S. J. Connon, Org. Lett., 2010,
12, 608-611.
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.
The generation of highly unstable chloromethylmagnesium chloride in a
continuous flow reactor and a subsequent reaction with aldehydes and ketones
provides chlorohydrins and epoxides in good yields within a total residence time
of only 2.6 s. The outcome of the reaction can be tuned by simply using either a
basic or an acidic quench.
T. von Keutz, D. Cantillo, C. O. Kappe,
Org. Lett., 2020, 22, 7537-7541.
Rhodium(II) acetate catalyzed reactions of phenyl- and styryldiazoacetates
with aldehydes, ketones, or imines enable stereospecific epoxidation and
aziridination via carbonyl ylide intermediates.
M. P. Doyle, W. Hu, D. J. Timmons,
Org. Lett., 2001, 3, 933-935.
A chiral titanium complex formed in situ from Ti(OiPr)4 and
chiral 1,16-dihydroxytetraphenylene with rigid conformation enables highly
diastereo- and enantioselective Darzens reactions between aldehydes and diazo-N,N-dimethylacetamide
to provide cis-glycidic amides in good yields with excellent enantiomeric
purities.
G.-L. Chai, J.-W. Han, H. N. C. Wong, Synthesis, 2017,
49, 181-187.
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.
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.
