Polycyclic phosphonic acid derivatives obtained by a [4+2] cycloaddition strategy using phosphonodienes

被引：12

作者：

Villemin, Elise ^{[1
]}

Robeyns, Koen ^{[1
]}

Robiette, Raphael ^{[1
]}

Herent, Marie-France ^{[2
]}

Marchand-Brynaert, Jacqueline ^{[1
]}

机构：

[1] Catholic Univ Louvain, ICMN, Mol Solids & React MOST, B-1348 Louvain, Belgium

[2] Catholic Univ Louvain, LDRI, B-1200 Brussels, Belgium

来源：

TETRAHEDRON | 2013年 / 69卷 / 03期

关键词：

1-Phosphonodienes; Diels-Alder reaction; Phosphonic acid; Horner-Wadsworth-Emmons reaction; Benzyl deprotection; MOLECULAR-ORBITAL METHODS; DIELS-ALDER REACTION; 1-PHOSPHONO-1,3-BUTADIENES; ISOMERIZATION; ESTERS; ROUTE;

D O I：

10.1016/j.tet.2012.11.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical route is described for the preparation of 1-phosphono-3(4-di)-substituted-1,3-butadienes based on the Horner-Wadsworth-Emmons (HWE) reaction. Their reactivity in the Diels-Alder (DA) reaction with three selected dienophiles is studied and compared to diethyl 1-phosphono-1,3-butadiene. A particular attention is given to the P-deprotection of cycloadducts from dibenzyl phosphonodienes. New phosphonated bicycles and tricycles have been obtained using this HWE/DA reaction sequence. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1138 / 1147

页数：10

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