کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5220801 | 1383399 | 2011 | 10 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
An unusual regiochemistry of reactions of a cyclohexenylphosphonate bearing a β-ethoxycarbonyl group with aldehydes
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
Reactions of lithiated ethyl 6-(dimethoxyphosphoryl)cyclohex-1-enecarboxylate with aliphatic, aromatic, and unsaturated aldehydes were studied and determined to proceed with α or δ regioselectivity. Such an unusual regioselectivity results from the contribution of two allylic carbanions: one, stabilized by the phosphonate moiety and the other stabilized by the carboethoxy group. The course of the reaction depends mainly on the structure of the aldehyde and the reaction conditions. The products of Horner–Wadsworth–Emmons reaction, including an analogue of some retinol metabolites, were formed under kinetic conditions whereas the δ-adducts were obtained as thermodynamic products.
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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 67, Issue 10, 11 March 2011, Pages 1938–1947
Journal: Tetrahedron - Volume 67, Issue 10, 11 March 2011, Pages 1938–1947