کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5228106 1383624 2008 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
α-Amino acids as acid components in the Passerini reaction: influence of N-protection on the yield and stereoselectivity
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
α-Amino acids as acid components in the Passerini reaction: influence of N-protection on the yield and stereoselectivity
چکیده انگلیسی

The Passerini reaction offers an easy access to depsipeptides, when both acid and isocyanide are derived from α-amino acids. However, racemisation of isocyanides derived from α-amino acid esters severely limits their use in the Passerini reaction. In order to overcome this limitation, a study on the influence of the α-amino acid N-protecting group on the yield and diastereoisomeric ratio of the product of the Passerini reaction was performed. Six different protecting groups were tested. Their influence turns out to be crucial and is not constant when the amino acid is changed. After optimisation, the Passerini reaction products with cyclohexanone as the carbonyl component were obtained with 99% yield and >98% de.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 64, Issue 41, 6 October 2008, Pages 9780-9783
نویسندگان
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