Categories: Synthesis of O-Heterocycles, C-O Bond Formation, Synthesis of cyclic ethers >
Synthesis of oxetanes
Name Reactions
Recent Literature
Divergent Photocatalytic Reactions of α-Ketoesters under Triplet
Sensitization and Photoredox Conditions
J. Zheng, X. Dong, T. P. Yoon,
Org. Lett., 2020, 22, 6510-6515.
The intramolecular O-vinylation of γ-bromohomoallylic alcohols with 10 mol % of CuI as the catalyst and 20 mol % of
1,10-phenanthroline as the ligand in refluxing MeCN led to the convenient formation of the corresponding
2-methyleneoxetanes in good to excellent yields via a 4-exo ring closure. 4-exo cyclization is preferred over other modes of cyclization.
Y. Fang, C. Li, J. Am. Chem. Soc., 2007,
129, 8092-8093.
An efficient solvent-controlled oxidative cyclization of Michael adducts of
malonates with chalcones with the combination of iodosobenzene and
tetrabutylammonium iodide enables the divergent synthesis of highly
functionalized oxetanes and cyclopropanes in good yields with high
diastereoselectivity.
Y. Ye, C. Zheng, R. Fan, Org. Lett., 2009,
11, 3156-3159.
3-(Silyloxy)oxetanes are obtained by irradiating mixtures of aromatic aldehydes
and silyl enol ethers in benzene as the solvent. Under similar conditions, but
in acetonitrile rather than benzene, the Paternò-Büchi reaction of N-acyl
enamines gives the corresponding protected 3-aminooxetanes. The reactions occur
with high diastereoselectivity.
F. Vogt, K. Jödicke, J. Schröder, T. Bach, Synthesis, 2009,
4268-4273.