Use of allenylphosphonates as new substrates for phosphane-catalyzed [3+2] and [4+2] annulations

被引：66

作者：

Panossian, Armen ^{[1
]}

Fleury-Bregeot, Nicolas ^{[1
]}

Marinetti, Angela ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, UPR 2301, F-91198 Gif Sur Yvette, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 22期

关键词：

phosphanes; organocatalysis; phosphonates; allenes; asymmetric catalysis;

D O I：

10.1002/ejoc.200800347

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The suitability of allenylphosphonates as substrates in phosphane-catalyzed annulation reactions has been investigated. Despite their lower reactivity relative to allenyl esters, allenylphosphonates overall display the anticipated behavior: pyrrolines, tetrahydropyridines, and cyclopentenes bearing phosphoryl functions were obtained from imines, alpha,beta-unsaturated esters, and enones in Bu3P- or iBu(3)P-promoted reactions. Enantio selective variants of these cyclization reactions afforded enantiomeric excesses of up to 90% when phosphepine A(2) was used as the chiral catalyst. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：3826 / 3833

页数：8

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