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学科主题: 天然产物有机化学
题名: Highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by asymmetric Mannich reaction and chiral recognition
其他题名: Highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by asymmetric Mannich reaction and chiral recognition
作者: Jiang B(姜标) ; Dong JJ(董家佳) ; Si YG(司玉贵) ; Zhao XL(赵小龙) ; Huang ZG(黄祚刚) ; Xu M(胥敏)
通讯作者: 姜标
刊名: Adv. Synth. Catal.
发表日期: 2008
卷: 350, 期:9, 页:1360-1366
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所
英文摘要: 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).
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000256976100028
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/20259
Appears in Collections:中科院天然产物有机化学重点实验室_期刊论文

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Recommended Citation:
Jiang B,Dong JJ,Si YG,et al. Highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by asymmetric Mannich reaction and chiral recognition[J]. Adv. Synth. Catal.,2008,350(9):1360-1366.
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