Stereoselective construction of highly functionalized azetidines via a [2 + 2]-cycloaddition.
A facile stereoselective synthesis of highly functionalized azetidines from a novel [2 + 2]-cycloaddition of 2-aminomalonates to chalcones is reported. The desired four-membered ring construction proceeded via a grind-promoted solvent-free Michael addition and a PhIO/Bu(4)NI mediated oxidative cyclization and afforded azetidines in moderate to good yields with excellent diastereoselectivities.
Ye
Yang
Y
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China, and Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials, Department of Chemistry, Fudan University, Shanghai 200433, China.
Wang
Hua
H
Fan
Renhua
R
D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D047188:Chalcones / Q000737:chemistry*; D003500:Cyclization; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001384:Azetidines; D047188:Chalcones; D008314:Malonates