In this work, α-phenyl-N-tert-butylnitrone (PBN), N-benzylidene-1-diethoxyphosphoryl-1-methylethylamine N-oxide (PPN) and N-benzylidene-1-ethoxycarbonyl-1-methylethylamine N-oxide (EPPN) derivatives bearing methoxy groups (MeO-) on the phenyl ring were sy
Stereoselective synthesis of fluoroalkenoates and fluorinated isoxazolidinones: N-substituents governing the dual reactivity of nitrones
α-Fluoroalkenoates and 4-fluoro-5-isoxazolidinones are of vast interest due to their potential biological applications. We now demonstrate the syntheses of (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones by the reactions between nitrones and α-fluoro-α-bromoacetate. By altering N-substituents in nitrones, (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones can be achieved, respectively, with high chemo- and stereoselectivities. Experimental and computational studies have been conducted to elucidate the reaction mechanisms. Linear free energy relationship studies further revealed that the N-substituent effects are primarily of electronic origin. Copyright
Prakash, G.K. Surya,Zhang, Zhe,Wang, Fang,Rahm, Martin,Ni, Chuanfa,Iuliucci, Marc,Haiges, Ralf,Olah, George A.
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p. 831 - 838
(2014/01/23)
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