کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5220894 1383403 2010 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Asymmetric catalytic aziridination of dihydronaphthalenes for the preparation of substituted 2-aminotetralins
چکیده انگلیسی

An enantioselective synthesis of substituted 2-aminotetralins from dihydronaphthalenes in four steps is described. The key step is the Jacobsen’s (diimine)copper-catalyzed asymmetric aziridination of dihydronaphthalenes to the respective aziridines in 33–82% yields and 60–87% enantiomeric excess. The enantioselectivity and the yield were dependent on the properties of the nitrene precursor. pTsNIPh appeared in general to give better results than pNsNIPh. Aziridines were ring-opened in the benzylic position by catalytic hydrogenolysis in quantitative yields, and deprotected in two steps to the respective 2-aminotetralins in 66–85% yields. The synthesis of (S)-2-aminotetralin (>98% ee) and (S)-2-amino-7-methoxytetralin (56% ee) were accomplished in 30 and 52% overall yields, respectively.

Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 66, Issue 52, 24 December 2010, Pages 9790–9797