Catalytic Asymmetric Inverse-Electron-Demand (IED) [4+2] Cycloaddition of Salicylaldimines: Preparation of Optically Active 4-Aminobenzopyran Derivatives

被引：49

作者：

Bernardi, Luca ^{[1
]}

Comes-Franchini, Mauro ^{[1
]}

Fochi, Mariafrancesca ^{[1
]}

Leo, Virginia ^{[1
]}

Mazzanti, Andrea ^{[1
]}

Ricci, Alfredo ^{[1
]}

机构：

[1] Univ Bologna, Dept Organ Chem A Mangini, I-40136 Bologna, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 18期

关键词：

asymmetric synthesis; cycloaddition; electron-rich alkenes; fused-ring systems; organic catalysis; CHIRAL BRONSTED ACID; DIELS-ALDER REACTIONS; ENE-TYPE REACTION; CIS-FUSED PYRANO; DIASTEREOSELECTIVE SYNTHESIS; ANTIHYPERTENSIVE ACTIVITY; ABSOLUTE-CONFIGURATIONS; CIRCULAR-DICHROISM; NATURAL-PRODUCTS; PHOSPHORIC-ACID;

D O I：

10.1002/adsc.201000608

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The catalytic asymmetric inverse-electron-demand (IED) [4+2] cycloaddition of various salicylaldehyde-derived N-arylimines with electron-rich alkenes in the presence of chiral BINOL-derived phosphoric acid catalysts has been studied with the aim of obtaining optically active 4-aminobenzopyran derivatives. Dienophiles such as 2,3-dihydro-2H-furan, benzyl N-vinylcarbamate and 2-vinylindole have been employed.

引用

页码：3399 / 3406

页数：8

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