Categories: Synthesis of N-Heterocycles, Synthesis of O-Heterocycles >
Synthesis of isoxazolidines
Recent Literature
A direct, highly efficient KOAc-catalyzed one-pot three-component reaction of
readily accessible diazo compounds, nitrosoarenes, and alkenes provides
functionalized isoxazolidines in high yields. The reaction offers cheap and
readily available catalyst and starting materials, excellent functional group
compatibility, wide substrate scope, and excellent chemo-, regio-, and
diastereoselectivities.
X. Li, T. Feng, D. Li, H. Chang, W. Gao, W. Wei, J. Org. Chem., 2019, 84,
4402-4412.
A general DBU/NBS-mediated one-pot three-component cycloaddition reaction of
easily accessible malonic acid derivatives, nitrosoarenes, and alkenes provides
direct access to highly functionalized isoxazolidine derivatives with very good
yields, broad functional group tolerance, and excellent regio- and
diastereo-selectivities under mild conditions.
X. Li, L. Zheng, X. Gong, H. Chang, W. Gao, W. Wei, J. Org. Chem., 2021, 86,
1096-1107.
The oxidative intramolecular bromo-amination of various N-alkenyl
sulfonamides and N-alkenoxyl sulfonamides via umpolung of alkali metal
bromides occurred exo-selectively to generate pyrrolidines and isoxazolidines
in high yields with good diastereoselectivities. This method provided the
desired products with a low amount of organic waste.
K. Moriyama, Y. Izumisawa, H. Togo, J. Org. Chem., 2011,
76, 7249-7255.
A chiral Ti(IV) catalyst can be successfully utilized in the asymmetric
1,3-dipolar cycloaddition reactions between various nitrones and acrolein to
give the corresponding endo cycloadducts (isoxazolidines) with high to
excellent enantioselectivities.
T. Kano, T. Hashimoto, K. Maruoka, J. Am. Chem. Soc., 2005, 70, 11926-11927.
A catalyst composed of Pd(OAc)2 and S-Phos allows the conversion
of aryl chlorides as electrophiles in Pd-catalyzed alkene carboamination and
carboetherification, minimizes N-arylation, and prevents formation of
regiosisomieric mixtures. Various heterocycles, including pyrrolidines,
isoxazolidines, tetrahydrofurans, and pyrazolidines, are efficiently generated
with this method.
B. R. Rosen, J. E. Ney, J. P. Wolfe, J. Org. Chem., 2010,
75, 2756-2759.
