کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5227590 1383611 2008 9 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Metal-mediated dearomatization leading to 2-azaspiro[4.5]decanes via tandem nucleophilic aromatic addition-Horner-Wadsworth-Emmons olefination-oxidative demetalation sequences
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Metal-mediated dearomatization leading to 2-azaspiro[4.5]decanes via tandem nucleophilic aromatic addition-Horner-Wadsworth-Emmons olefination-oxidative demetalation sequences
چکیده انگلیسی

A ruthenium-mediated dearomatization sequence has been developed that delivers structurally intriguing azaspirolactam products in stereoselective fashion. Treatment of (η6-arene)Ru(cyclopentadienyl) complexes bearing N-benzyl-β-amido phosphonate side chains with excess NaH results in intramolecular nucleophilic aromatic addition to the ipso position of the coordinated arenes. Subsequent Horner-Wadsworth-Emmons (HWE) reaction with added aldehydes affords olefinated spirolactam cyclohexadienyl ruthenium complexes. Mild oxidation with CuCl2 or CuBr2 under CO effects removal and recovery of the CpRu(II) fragment. Substituents present on the cyclohexadienyl skeleton influence the outcome of demetalation and products obtained in this study include functionalized 2-azaspiro[4.5]decanes and tetrahydroisoquinolinones.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 64, Issue 44, 27 October 2008, Pages 10123-10131
نویسندگان
, ,