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

被引：182

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

页码：8666 / 8669

页数：4

共 36 条

[1] Asymmetric construction of quaternary carbon stereocenters: High stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes [J].