Enantioselective Friedel-Crafts Reaction of Indoles with Trifluoroacetaldehyde Catalyzed by Cinchona Alkaloids

被引：26
|
作者：
Borkin, Dmitry A. [1 ]
Landge, Shainaz M. [1 ]
Toeroek, Bela [1 ]
机构：
[1] Univ Massachusetts, Dept Chem, Boston, MA 02125 USA
来源：
CHIRALITY | 2011年 / 23卷 / 08期
关键词：
enantioselective; organocatalysis; Cinchona; indole; fluoral; chiral trifluoromethylated alcohols; REVERSE-TRANSCRIPTASE INHIBITOR; ASYMMETRIC-SYNTHESIS; PROCHIRAL KETONE; ALDOL REACTION; TRIFLUOROMETHYLATION; ENOLATE;
D O I：
10.1002/chir.20982
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The first direct asymmetric synthetic preparation of trifluoro-1-(indol-3-yl)ethanols (TFIEs) is described by an enantioselective organocatalytic method from indoles and inexpensive trifluoroacetaldehyde methyl hemiacetal. The reaction is catalyzed by hydroquinine to produce TFIEs in an almost quantitative yield and with enantioselectivities up to 75% at room temperature. The enantioselectivity is strongly dependent on the concentration of substrates and catalyst due to the competitive noncatalyzed reaction. Chirality 23:612-616, 2011. (C) 2011 Wiley-Liss, Inc.
引用
收藏
页码：612 / 616
页数：5
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