Synthesis of novel C2-symmetric chiral crown ethers and their application to enantioselective trifluoromethylation of aldehydes and ketones

被引：34

作者：

Kawai, Hiroyuki ^{[1
]}

Kusuda, Akihiro ^{[1
]}

Mizuta, Satoshi ^{[1
]}

Nakamura, Shuichi ^{[1
]}

Funahashi, Yasuhiro ^{[1
]}

Masuda, Hideki ^{[1
]}

Shibata, Norio ^{[1
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2009年 / 130卷 / 08期

关键词：

Trifluoromethylation; Crown ethers; Chiral catalysis; Enantioselective; Phase-transfer catalysts; HOST-GUEST COMPLEXATION; ASYMMETRIC ALDOL REACTIONS; NUCLEOPHILIC TRIFLUOROMETHYLATION; CATALYZED TRIFLUOROMETHYLATION; CARBONYL-COMPOUNDS; RECOGNITION;

D O I：

10.1016/j.jfluchem.2009.06.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Synthesis of novel C2-symmetric chiral crown ethers and their application to enantioselective trifluoromethylation of aldehydes and ketones are discussed. The use of a series of C2-symmetric chiral crown ethers 2 or 3 derived from commercially available (R)-1,1'-bi-2-naphthol for the enantioselective trifluoromethylation of 2-naphthyl aldehyde 1a with (trifluoromethyl)trimethylsilane in the presence of a base was attempted. Iodo-substituted crown ether 2b was found to be the most effective in the model reaction. Moderate enantioselectivities were observed for the trifluoromethylation of both aryl or alkyl aldehydes and alkyl aryl ketones in 21-44% ees. Although the ees are still improvable, this is the first example of a chiral crown ether-catalyzed enantioselective trifluoromethylation reaction. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：762 / 765

页数：4

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