Cinchona-alkaloid-catalyzed enantioselective direct aldol-type reaction of oxindoles with ethyl trifluoropyruvate

被引：181
|
作者：
Ogawa, Shinichi
Shibata, Norio [1 ]
Inagaki, Junji
Nakamura, Shuichi
Toru, Takeshi
Shiro, Motoo
机构：
[1] Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan
[2] Rigaku Corp, Tokyo 1968666, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 45期
关键词：
asymmetric catalysis; cinchona alkaloids; heterocycles; organocatalysis; trifluoromethyl alcohols;
D O I：
10.1002/anie.200703317
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) One or t'other: Pseudoenantiomeric cinchona alkaloids can be used as organocatalysts to access both enantiomeric products of the title reaction selectively in high yields with high diastereo- and enantioselectivities (up to 99% ee; see scheme). One of the two contiguous quaternary stereogenic carbon centers that are constructed simultaneously is a pharmaceutically significant tertiary α-trifluoromethyl alcohol center. R1 = alkyl; R2 = H, Me. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：8666 / 8669
页数：4
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