کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5273621 | 1385494 | 2012 | 4 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Ireland-Claisen rearrangement of secondary allyl acetate revisited: inevitable C-silylation circumvented by one-pot application of excessive LDA/TMSCl and TBAF
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
Yield lowering C-silylation was found to be inevitable in all the six tested examples of stoichiometric LDA/TMSCl promoted Ireland-Claisen rearrangement of secondary allyl acetates. In order to circumvent this problem, a higher yielding protocol was devised after the isolated by-products were found to be excellent substrates for further rearrangement. Thus, excessive LDA/TMSCl was applied to achieve complete 3,3â²-sigmatropic shift of the substrates, and the resulting mixtures of normal and α-silylated γ,δ-unsaturated carboxylic acids was then desilylated by one-pot application of TBAF.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 53, Issue 17, 25 April 2012, Pages 2177-2180
Journal: Tetrahedron Letters - Volume 53, Issue 17, 25 April 2012, Pages 2177-2180
نویسندگان
Di Liu, Xiaoming Yu,