کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5285741 1385765 2006 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
SmI2-Promoted novel tandem elimination and coupling reactions of aliphatic imides with carbonyl compounds: application to the synthesis of dl-isoretronecanol
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
SmI2-Promoted novel tandem elimination and coupling reactions of aliphatic imides with carbonyl compounds: application to the synthesis of dl-isoretronecanol
چکیده انگلیسی
Treatment of α-hetero-substituted cyclic imides with carbonyl compounds mediated by samarium(II) diiodide in the presence of HMPA was found to undergo novel tandem elimination and reductive coupling reactions to generate α-hydroxyalkylated imides in good to high yields. Stereochemistry of the coupling products was researched and the result that increasing the steric bulkiness of the N-substituents leads to an increase of threo-selectivity was observed. The mechanistic origins of this stereoselectivity are also briefly documented and the reaction was further applied to the convenient synthesis of a simple pyrrolizidine alkaloid, isoretronecanol.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 47, Issue 10, 6 March 2006, Pages 1607-1611
نویسندگان
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