Caddick Stephen, Bush Hannah D
Centre for Biomolecular Design and Drug Development, The Chemistry Laboratory, University of Sussex, Falmer, Brighton BN1 9QJ, UK.
Org Lett. 2003 Jul 10;5(14):2489-92. doi: 10.1021/ol0347388.
[reaction: see text] An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectivity. Subsequent amine displacement of the PFP moiety furnished functionalized sulfonamide products in good yields.
[反应:见正文] 描述了各种硝酮与五氟苯基(PFP)乙烯基磺酸盐的高效分子间1,3-偶极环加成反应。该转化反应生成了具有前所未有的立体和区域选择性的稳定“反向”环加成产物。随后,PFP部分被胺取代,以良好的产率得到了功能化的磺酰胺产物。