کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5266422 | 1385310 | 2013 | 4 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Synthesis of β-hydroxy-δ-trichloromethyl-δ-valerolactones by intramolecular samarium/ytterbium diiodide-mediated Reformatsky reaction
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
The synthesis of α-methyl-β-hydroxy-δ-trichloromethyl-δ-valerolactone was achieved by an intramolecular Reformatsky reaction. The cyclisation was effected by samarium diiodide or (for the first time) ytterbium diiodide. The diastereoselectivity of the reaction corresponds to earlier investigations by Molander. Consecutive stereoselective reactions during the esterification to the Reformatsky precursor 1,1,1-trichloropent-4-en-2-yl 2-bromopropanoate and in the Reformatsky reaction itself led to (3RS,4RS,6SR)-4-hydroxy-3-methyl-6-(trichloromethyl)tetrahydro-2H-pyran-2-one (3a) as the major formed diastereomer. The influence of the orientation of the substituents in the transition state is discussed.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 54, Issue 8, 20 February 2013, Pages 921-924
Journal: Tetrahedron Letters - Volume 54, Issue 8, 20 February 2013, Pages 921-924
نویسندگان
Thies M. Schulze, Jörg Grunenberg, Stefan Schulz,