Highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by asymmetric Mannich reaction and chiral recognition

被引：77

作者：

Jiang, Biao ^{[1
]}

Dong, Jia Jia ^{[1
]}

Si, Yu Gui ^{[1
]}

Zhao, Xiao Long ^{[1
]}

Huang, Zuo Gang ^{[1
]}

Xu, Min ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 09期

关键词：

C-C coupling; HIV therapeutics; hydrogen bonds; organocatalysis; self-discrimination;

D O I：

10.1002/adsc.200800039

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by an asymmetric Mannich reaction and chiral recognition are described. The key transformation was to establish the chiral trifluoromethyl quaternary carbon center by a diamine-Bronsted acid-catalyzed enantioselective and regioselective Mannich reaction of a methyl ketone and 4-trifluoromethyldihydroquinazo-line. An unusual phenomenon of self-discrimination of enantiomers in hydrogen-bonded dimers was observed. A valuable intermediate was transformed into the enantiopure HIV reverse transcriptase inhibitor DPC 083 (> 99.9 ee) simply by reduction of the carbonyl group and elimination of the hydroxy group in hexamethylphosphoric tramide (HMPA).

引用

页码：1360 / 1366

页数：7

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