Novel chiral 1-phosphono-1,3-butadiene for asymmetric hetero Diels-Alder cycloadditions with nitroso and azodicarboxylate dienophiles

被引：19

作者：

Monbaliu, Jean-Christophe ^{[1
]}

Tinant, Bernard ^{[2
]}

Peeters, Daniel ^{[2
]}

Marchand-Brynaert, Jacqueline ^{[1
]}

机构：

[1] Catholic Univ Louvain, Dept Chim, Unite Chim Organ & Med, B-1348 Louvain, Belgium

[2] Catholic Univ Louvain, Dept Chim, Unite Chim Struct & Mecanismes Reactionnels, B-1348 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 07期

关键词：

Chiral phosphonodienes; Nitroso dienophiles; Azodicarboxylate dienophiles; Hetero Diels-Alder reaction; DFT calculation; HETERODIENOPHILES; REACTIVITY;

D O I：

10.1016/j.tetlet.2009.12.063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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/6-31G** 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. (C) 2009 Elsevier Ltd All rights reserved.

引用

页码：1052 / 1055

页数：4

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