Proline as Lewis base catalyst: diastereoselective synthesis of isoxazoline-N-oxide through [3 + 2] cycloaddition.
A catalytic cascade synthesis of isoxazoline-N-oxide was developed through proline-catalyzed nitroalkene activation. A large substrate scope was obtained with good to excellent yields. Mechanistic studies revealed intramolecular cyclization as the rate-determining step, giving only trans isomers in all cases.
Duan
Haifeng
H
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Sun
Xiaohua
X
Liao
Wenyan
W
Petersen
Jeffrey L
JL
Shi
Xiaodong
X
D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014753:Vinyl Compounds / Q000737:chemistry
D003497:Cyclic N-Oxides; D004952:Esters; D007555:Isoxazoles; D014753:Vinyl Compounds; D011392:Proline