کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5270617 | 1385421 | 2010 | 4 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Novel chiral 1-phosphono-1,3-butadiene for asymmetric hetero Diels-Alder cycloadditions with nitroso and azodicarboxylate dienophiles
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
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چکیده انگلیسی
Chiral 1-phosphonodienes bearing a bicyclic (R,R)-1,3,2-dioxaphospholane or a (R,R)-1,3,2-diazaphospholidine auxiliary are potent dienes for asymmetric hetero Diels-Alder reactions. Their reactivity towards model nitroso and azodicarboxylate dienophiles has been studied by means of theoretical chemistry at the B3LYP/6-31Gââ level. This model, taking solvent effects into account, allowed us to identify parameters governing the stereoselectivity of this reaction. Our study emphasizes a synergy effect when increasing the steric hindrance of substituents of both partners. This led us to predict high levels of diastereoselectivity for one diene. Accordingly, we have hereby illustrated a convenient and original synthesis of this diene and its cycloadditions with commercially available nitroso and azodicarboxylate dienophiles.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 51, Issue 7, 17 February 2010, Pages 1052-1055
Journal: Tetrahedron Letters - Volume 51, Issue 7, 17 February 2010, Pages 1052-1055
نویسندگان
Jean-Christophe Monbaliu, Bernard Tinant, Daniel Peeters, Jacqueline Marchand-Brynaert,