Categories: Synthesis of O-Heterocycles, C-O Bond Formation, Synthesis of cyclic ethers >
Synthesis of cyclic ethers
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| Epoxides |
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| Tetrahydro- furans |
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Tetrahydro- pyrans |
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Recent Literature
The platinum-catalyzed hydroalkoxylation of γ- and δ-hydroxy olefins
tolerated various substitution patterns and a number of functional groups
including pivaloate and acetate esters, amides, silyl and benzyl ethers, and
pendant hydroxyl and olefinic groups.
H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc.,
2004, 126, 9536-9537.
The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room
temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield
and stereoselectivity. Various fragrant compounds have been synthesized using
this method.
E. J. Alvarez-Manzaneda, R. Chabouna, E. Alvarez, E. Cabrera, R.
Alvarez-Manzaneda, A. Haidour, J. M. Ramos, Synlett, 2006,
1756-1758.
The Au(I)-catalyzed intramolecular hydroamination of N-allenyl
carbamates was effective for the formation of various cyclic amines. γ-Hydroxy
and δ-hydroxy allenes underwent Au-catalyzed intramolecular
hydroalkoxylation to form the corresponding
oxygen heterocycles in good yield. 2-Allenyl indoles
underwent Au-catalyzed intramolecular hydroarylation to form 4-vinyl tetrahydrocarbazoles in good yield.
Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc.,
2006, 128, 9066-9073.
Treatment of 3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones
with diisobutylaluminum hydride at -78 °C followed by acid quenching
furnishes spiro ethers, whereas the corresponding 3-(carboxyalkyl)-substituted
cycloalkenones generate spiro lactones upon reaction with sodium borohydride
at 30 °C followed by acid quenching.
M.-C. P. Yeh, Y.-C. Lee, T.-C. Young, Synthesis, 2006, 3621-3624.
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.
Dehydration of 1,6-diols by treatment with BF3·OEt2 in
dichloromethane gave tetrahydrobenzoxepines in very good yields, whereas
1,7-diols did not undergo dehydration.
M. Yus, T. Soler, F. Foubelo, Tetrahedron, 2002, 58,
7009-7016.
An efficient and regioselective Yb(OTf)3-promoted
palladium-catalyzed oxidative cyclization of γ-heteroalkenyl β-keto amides
has been developed. Under simple aerobic condition, various six-, seven-,
and eight-membered-ring N- and O-heterocycles were obtained in excellent yield.
K.-T. Yip, J.-H. Li, O.-Y. Lee, D. Yang, Org. Lett.,
2005, 7, 5717-5719.
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Diastereoselective and Enantioselective Construction of Cyclic Ethers Stereocontrolled Construction of Cyclic Ethers Enantioselective Construction of Naturally-Occurring Cyclic Ethers |
