Asymmetric Bronsted Acid Catalysis: Catalytic Enantioselective Synthesis of Highly Biologically Active Dihydroquinazolinones

被引：201

作者：

Rueping, Magnus ^{[1
]}

Antonchick, Andrey P. ^{[1
]}

Sugiono, Erli ^{[1
]}

Grenader, Konstantin ^{[1
]}

机构：

[1] Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 05期

关键词：

antitumor agents; inhibitors; organocatalysis; phosphoric acid diester; FRIEDEL-CRAFTS REACTION; DIELS-ALDER REACTION; VINYLOGOUS MANNICH REACTION; CHIRAL PHOSPHORIC-ACID; N-ACYL IMINES; TRANSFER HYDROGENATION; 1,3-DICARBONYL COMPOUNDS; REDUCTIVE AMINATION; KINETIC RESOLUTION; ANTICANCER DRUGS;

D O I：

10.1002/anie.200804770

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Surprisingly straightforward: A metal-free, highly enantioselective Brønsted acid catalyzed condensation/addition reaction has been developed for the construction of 2,3-dihydroquinazolinones starting from 2-aminobenzamide and aldehydes (see scheme). This efficient approach provides 2,3-dihydroquinazolinones with a strong preference for the S enantiomers, which have higher biological activities than the R enantiomers. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：908 / 910

页数：3

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