Copper(II) triflate-bis(oxazoline)-catalysed enantioselective electrophilic fluorination of β-ketoesters

被引：145

作者：

Ma, JA ^{[1
]}

Cahard, D ^{[1
]}

机构：

[1] Univ Rouen, IRCOF, CNRS, UMR 6014, F-76821 Mont St Aignan, France

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 06期

关键词：

D O I：

10.1016/j.tetasy.2004.01.014

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new efficient catalytic enantioselective electrophilic fluorination of cyclic and acyclic beta-ketoesters is developed. As low as 1 mol % of chiral bis(oxazoline)-copper triflate complexes catalyses the fluorination by means of N-fluorobenzenesulfonimide. The use of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) is crucial for achieving high enantio selectivity. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1007 / 1011

页数：5

共 31 条

[1] Enantioselective electrophilic fluorination in ionic liquids [J].

Baudequin, C ;

Plaquevent, JC ;

Audouard, C ;

Cahard, D .

GREEN CHEMISTRY, 2002, 4 (06) :584-586

[2] Catalytic asymmetric protonation of fluoro-enolic species:: access to optically active 2-fluoro-1-tetralone [J].

Baur, MA ;

Riahi, A ;

Hénin, F ;

Muzart, J .

TETRAHEDRON-ASYMMETRY, 2003, 14 (18) :2755-2761

[3] Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents:: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF4) [J].

Cahard, D ;

Audouard, C ;

Plaquevent, JC ;

Roques, N .

ORGANIC LETTERS, 2000, 2 (23) :3699-3701

[4] N-Fluorocinchonidinium tetrafluoroborate F-CD-BF4:: purification and structure elucidation of this novel enantioselective electrophilic fluorinating agent [J].

Cahard, D ;

Audouard, C ;

Plaquevent, JC ;

Toupet, L ;

Roques, N .

TETRAHEDRON LETTERS, 2001, 42 (10) :1867-1869

[5]

CAHARD D, PLAQUEVENT J C

[6] DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX [J].

COREY, EJ ;

IMAI, N ;

ZHANG, HY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :728-729

[7] Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes [J].

Evans, DA ;

Scheidt, KA ;

Johnston, JN ;

Willis, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4480-4491

[8] C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic enantioselective Michael addition of silylketene acetals to alkylidene malonates [J].

Evans, DA ;

Rovis, T ;

Kozlowski, MC ;

Tedrow, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) :1994-1995

[9] Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters [J].

Frantz, R ;

Hintermann, L ;

Perseghini, M ;

Broggini, D ;

Togni, A .

ORGANIC LETTERS, 2003, 5 (10) :1709-1712

[10] Immobilization and reuse of Pd complexes in ionic liquid:: Efficient catalytic asymmetric fluorination and Michael reactions with β-ketoesters [J].

Hamashima, Y ;

Takano, H ;

Hotta, D ;

Sodeoka, M .

ORGANIC LETTERS, 2003, 5 (18) :3225-3228

← 1 2 3 4 →