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

被引：202
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
收藏
页码：908 / 910
页数：3
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