Enantioselective electrophilic trifluoromethylation of β-keto esters with Umemoto reagents induced by chiral nonracemic guanidines

被引：64

作者：

Noritake, Shun ^{[1
]}

Shibata, Norio ^{[1
]}

Nomura, Yoshinori ^{[1
]}

Huang, Yiyong ^{[1
]}

Matsnev, Andrej ^{[1
]}

Nakamura, Shuichi ^{[1
]}

Toru, Takeshi ^{[1
]}

Cahard, Dominique ^{[2
]}

机构：

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

[2] Univ & INSA Rouen, COBRA, CNRS, UMR 6014, F-76130 Mont St Aignan, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 17期

关键词：

ORGANOCATALYTIC ALPHA-FLUORINATION; CATALYTIC ASYMMETRIC FLUORINATION; N-FLUOROAMMONIUM SALTS; SILYL ENOL ETHERS; CINCHONA ALKALOIDS; 1,3-DICARBONYL COMPOUNDS; MICHAEL REACTION; IONIC LIQUID; AGENTS; COMBINATIONS;

D O I：

10.1039/b909641h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral nonracemic guanidines act as Bronsted bases to generate guanidinium enolates for the enantioselective electrophilic trifluoromethylation of beta-keto esters by means of S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate (Umemoto reagent) with good enantioselectivity of 60-70% range. Despite the fact that the ees are still improvable, the model reported in this work could spark the imagination of chemists to design new chiral bases to improve the stereochemical outcome.

引用

页码：3599 / 3604

页数：6

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