کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5230031 | 1383679 | 2007 | 9 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Regioselective cleavage of 3,4-epoxy alcohols with substituted alkynylaluminum reagents: application to the stereoselective synthesis of polypropionates
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
The reaction of 3-O-substituted propynyl aluminum reagents with a TIPS-protected 2,3-epoxy alcohol and several diastereomeric 2-methyl-3,4-epoxy alcohols offers a convenient synthetic approach for the subsequent preparation and epoxidation of allylic alcohols. The yields are low to moderate and the regioselectivity (internal vs external attack) is similar to that of the standard diethylpropynyl aluminum reagent. The TMS-acetylide alane reagent gives improved yields and good regioselectivity, and is the reagent of choice for the cleavage of the hindered epoxides. This attractive methodology is applied to the elaboration of two advanced polypropionate precursor fragments.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 63, Issue 34, 20 August 2007, Pages 8218-8226
Journal: Tetrahedron - Volume 63, Issue 34, 20 August 2007, Pages 8218-8226
نویسندگان
Wilnelia Dávila, Wildeliz Torres, José A. Prieto,