کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5283661 | 1385720 | 2007 | 5 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
The first synthesis of N,O-protected β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (SR)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformationally restrained β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1â²-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1â²-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-β-lactams. The synthesis of a dipeptide by reaction coupling between the 1â²-aminodioxolanone (2S,5R,1â²R)-19 and N,N-dimethylglycine was successfully achieved.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 48, Issue 29, 16 July 2007, Pages 5081-5085
Journal: Tetrahedron Letters - Volume 48, Issue 29, 16 July 2007, Pages 5081-5085
نویسندگان
Andrea Guerrini, Greta Varchi, Cristian Samorì, Rizzo Daniele, Battaglia Arturo,