New Cyclotrimerization of Aldehydes to Cyclopentenone or Tetrahydrofuran Induced by Dibromotriphenylphosphorane

被引：7

作者：

Heck, Marie-Pierre ^{[1
]}

Matt, Christophe ^{[2
]}

Wagner, Alain ^{[2
]}

Toupet, Loic ^{[3
]}

Mioskowski, Charles ^{[1
,2
]}

机构：

[1] CEA, iBiTecS, Serv Chim Bioorgan & Marquage, F-91191 Gif Sur Yvette, France

[2] Univ Strasbourg, Lab Syst Chim Fonct, Fac Pharm, F-67401 Illkirch Graffenstaden, France

[3] Univ Rennes 1, Inst Phys, UMR 6251, F-35042 Rennes, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 05期

关键词：

Aldehydes; Aldol reactions; Cyclotrimerization; Phosphorus; ALDOL-TISHCHENKO REACTION; TRIMERIZATION; ACETALDEHYDE; CHEMISTRY; CATALYST; SYSTEMS; ROUTE;

D O I：

10.1002/ejoc.200901105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Mono- or alpha-dialkylated aldehydes undergo cyclotrimerization in the presence of dibromotriphenylphosphorane (PPh3Br2) to afford cyclopentenones or tetrasubstituted tetrahydrofurans in good yields. These transformations proceed by a tandem aldol dimerization/Nazarov reaction or a tandem aldol dimerization/Prins cyclization.

引用

页码：966 / 971

页数：6

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