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Joanna Gajewiak 《Tetrahedron letters》2006,47(43):7607-7609
Lysophosphatidic acid (LPA) and phosphatidic acid (PA) are potent bioactive lipid mediators of signal transduction and are inactivated by phosphatases. To obtain receptor-isoform selective ligands with neutral phosphomimetic head groups, we performed the stereoselective synthesis of LPA and PA analogues with trifluoromethanesulfonamide and trifluoromethanesulfonamidoxy moieties replacing the phosphomonoester. 相似文献
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1,5-Hexadiene reacts with trifluoromethanesulfonamide in the oxidative system (t-BuOCl+NaI) to give trans-2,5-bis(iodomethyl)-1-(trifluoromethylsulfonyl)pyrrolidine 5 and 3,8-bis(trifluoromethylsulfonyl)-3,8-diazabicyclo[3.2.1]octane 6. With arenesulfonamides ArSO2NH2 (Ar=Ph, Tol), the reaction stops at the formation of the trans and cis isomers of 2,5-bis(iodomethyl)-1-(arenesulfonyl)pyrrolidine 7 and 8 (1:1). The cis isomers of 7 and 8 do not undergo cyclization to the corresponding 3,8-disubstituted 3,8-diazabicyclo[3.2.1]octanes. The reaction with triflamide represents the first example of one-pot two-step route to 3,8-diazabicyclo[3.2.1]octane system. 相似文献
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Mikhail Yu. Moskalik Vera V. Astakhova Uwe Schilde Irina V. Sterkhova Bagrat A. Shainyan 《Tetrahedron》2014
Reaction of trifluoromethanesulfonamide (triflamide) CF3SO2NH2 with 2,3-dimethylbuta-1,3-diene (2) and 2,5-dimethylhexa-2,4-diene (3) in the oxidative system (t-BuOCl+NaI) results in the formation of 2,4-dimethyl- or 2,2,4,4-tetramethyl-3,6-bis(triflyl)diazabicyclo[3.1.0]hexane through two successive heterocyclizations. Reaction of diene (3) with arenesulfonamides ArSO2NH2 (Ar=Ph, Tol), stops at the formation of the product of oxidative 1,4-addition, N,N′-(2,3-dimethylbut-2-ene-1,4-diyl)diarenesulfonamides, providing evidence of the essential difference between the reactivity of triflamide and arenesulfonamides. 相似文献
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Karen Thai 《Tetrahedron letters》2009,50(47):6540-6542
Unsymmetrical di- and trisubstituted triflyl guanidines are accessed through a simple, one-pot protocol from the corresponding isothiocyanate and amine. Furthermore, in the presence of base, trisubstituted triflyl guanidines are alkylated to obtain tetrasubstituted triflyl guanidines in high yields and complete regioselectivity. 相似文献
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Density functional theory calculations at the B3LYP/6-31G(d,p) level of theory were performed on the members of the isoelectronic series CF3SO2X (X=F, OH, NH2, CH3), in order to obtain the optimized geometric parameters and conformations for the four molecules, as well as the wavenumbers corresponding to the normal modes of vibration and the associated force constants. The original force field was transformed to local symmetry coordinates and scaled to reproduce the experimental wavenumbers. The trends observed in geometrical parameters and force constants along the isoelectronic series could be explained making use of the calculated atomic charges. 相似文献
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