90331-02-5Relevant articles and documents
Stereoselective synthesis of fluoroalkenoates and fluorinated isoxazolidinones: N-substituents governing the dual reactivity of nitrones
Prakash, G.K. Surya,Zhang, Zhe,Wang, Fang,Rahm, Martin,Ni, Chuanfa,Iuliucci, Marc,Haiges, Ralf,Olah, George A.
supporting information, p. 831 - 838 (2014/01/23)
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
Nitrone derivatives
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, (2008/06/13)
A compound represented by the figure (1) or a pharmaceutically acceptable salt thereof is useful as medicament for treating retinal degenerative disorders: wherein Ar is optionally substitued phenyl or optionally substituted heteroaryl;. n is 0, 1 or 2; W
1-AZADIENES AS A SYNTHON FOR HETEROCYCLIC SYNTHESIS
Ohshiro, Yoshiki,Komatsu, Mitsuo,Uesaka, Masatoshi,Agawa, Toshio
, p. 549 - 559 (2007/10/02)
1-Azabutadienes 1 were found to be a good building block for three- to five-membered heterocycles having a functional group.Oxidation of 1 with mCPBA afforded 3-alkenyloxaziridines 2.Cycloaddition of 1 with ketenes gave the 4-alkenylazetidinones 6.Addition of a nitrile imine occured across the C=N bond to give the 3-alkenyltriazoline 8, while that of a nitrile ylide occurred on the C=C bond to give the 3-formylpyrrole 14 formed by hydrolysis of the C=N bond.