Categories: Synthesis of N-Heterocycles, Synthesis of O-Heterocycles >
Synthesis of isoxazolidines
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.