Categories: Synthesis of O-Heterocycles, C-O Bond Formation >
Synthesis of butenolides
Related: |
 |
|
Recent Literature
The ruthenium-catalyzed
ring-closing metathesis of methallyl acrylates gave 4-Methyl-5-alkyl-2(5H)-furanones
in good to high yields. Despite the electron deficiency of both double bonds in
the starting acrylates, the first-generation
Grubbs' catalyst proved to be an effective catalyst for the ring closure.
M. Bassetti, A. D'Annibale, A. Fanfoni, F. Minissi, Org. Lett., 2005, 7, 1805-1808.
A new and convenient one-pot catalytic addition-elimination reaction converted a
range of (E)-3-butenoic acids into the corresponding butenolides in good
yields in the presence of 5 mol % diphenyl diselenide and [bis(trifluoroacetoxy)iodo]benzene
in acetonitrile.
D. M. Browne, O. Niyomura, T. Wirth, Org. Lett., 2007,
9, 3169-3171.
A sequential rhodium-catalyzed addition/lactonization reaction of organoboron
derivatives to alkyl 4-hydroxy-2-alkynoates allows the synthesis of 4-aryl/heteroaryl/vinyl-2(5H)-furanones
with an excellent control of regio- and chemoselectivity.
M. Alfonsi, A. Arcadi, M. Chiarini, F. Marinelli, J. Org. Chem., 2007,
72, 9510-9517.
Tetronic acids substituted by various groups were synthesized in one pot from
the corresponding aryl- or heteroarylacetic acid esters and hydroxyacetic acid
esters, by a tandem process involving a transesterification and a subsequent
Dieckmann cyclization.
A. Mallinger, T. Le Gall, C. Mioskowski, Synlett, 2008,
386-388.
A one-pot, convenient and general access to 5-sp2-substituted and
5,5-disubstituted tetronic acids embodies two consecutive chemical events: a
Michael addition of pyrrolidine on a secondary or tertiary γ-hydroxy-α,β-alkynyl
ester derivative to give the corresponding enamine, and a subsequent
acid-catalyzed hydrolysis-lactonization.
D. Tejedor, A. Santos-Expósito, F. García-Tellado, Synlett, 2006,
1607-1609.
A highly efficient carbon-carbon triple bond cleavage reaction of (Z)-enynols
offered a new route to highly substituted butenolides through a
gold(I)-catalyzed tandem cyclization/oxidative cleavage.
Y. Liu, F. Song, S. Guo, J. Am. Chem. Soc., 2006, 128, 11332-11333.
γ-Methylene-α,β-unsaturated γ-lactones were efficiently synthesized by a
Pd-catalyzed cyclization of 3,4-alkadienoic acids. The use of a N2
atmosphere ensures a high purity of the products.
S. Ma, F. Yu, Tetrahedron, 2005,
61, 9896-9901.
The facile iodolactonisation of ethyl 2,3-allenoates with I2 in aqueous MeCN
gave 4-iodofuran-2(5H)-ones in moderate to
high yields.
C. Fu, S. Ma, Eur. J. Org. Chem., 2005,
3942-3945.
| Related |
