Enantioselective electrophilic fluorination: a study of the fluorine-transfer from achiral N-F reagents to cinchona alkaloids

被引：38

作者：

Baudequin, C ^{[1
]}

Loubassou, JF ^{[1
]}

Plaquevent, JC ^{[1
]}

Cahard, D ^{[1
]}

机构：

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

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2003年 / 122卷 / 02期

关键词：

N-fluoro compounds; transfer fluorination; enantioselective electrophilic fluorination; ionic liquids;

D O I：

10.1016/S0022-1139(03)00085-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A transfer fluorination on cinchona alkaloids with the aid of achiral N-F fluorine-transfer reagents is described. Ten commercially available reagents were evaluated. Selectfluors(TM) 9 and 10, Accufluor(TM) 11, N-fluorobenzenesulfonimide (NFSi) 13, and N-fluoro-2,6-dichloropyridinium tetrafluoroborate 17 are effective fluorine-transfer reagents. The N-fluoroammonium salts of cinchona alkaloids thus prepared were employed in the construction of stereogenic fluorinated carbon centers with enantioselectivity as high as 85%. We also demonstrated that ionic liquids are effective "green" solvents for the development of this methodology. (C) 2003 Published by Elsevier Science B.V.

引用

页码：189 / 193

页数：5

共 24 条

[1] N-HALOGENO COMPOUNDS .14. TRANSFER FLUORINATION OF QUINUCLIDINE USING F-TEDA-BF4 (SELECTOR(TM) REAGENT) - LABORATORY SYNTHESIS OF N-FLUOROQUINUCLIDINIUM SALTS NOT REQUIRING THE USE OF ELEMENTAL FLUORINE
ABDULGHANI, M
BANKS, RE
BESHEESH, MK
SHARIF, I
SYVRET, RG
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1995, 73 (02) : 255 - 257
[2] Enantioselective electrophilic fluorination in ionic liquids
Baudequin, C
Plaquevent, JC
Audouard, C
Cahard, D
[J]. GREEN CHEMISTRY, 2002, 4 (06) : 584 - 586
[3] Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents:: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF4)
Cahard, D
Audouard, C
Plaquevent, JC
Roques, N
[J]. 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
Cahard, D
Audouard, C
Plaquevent, JC
Toupet, L
Roques, N
[J]. TETRAHEDRON LETTERS, 2001, 42 (10) : 1867 - 1869
[5] Asymmetric fluorination of enolates with nonracemic N-fluoro-2,10-camphorsultams
Davis, FA
Zhou, P
Murphy, CK
Sundarababu, G
Qi, HY
Han, W
Przeslawski, RM
Chen, BC
Carroll, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) : 2273 - 2280
[6] ASYMMETRIC FLUORINATION OF ENOLATES WITH N-FLUORO 2,10-(3,3-DICHLOROCAMPHORSULTAM)
DAVIS, FA
ZHOU, P
MURPHY, CK
[J]. TETRAHEDRON LETTERS, 1993, 34 (25) : 3971 - 3974
[7] NEW FLUORINATING REAGENTS .1. THE 1ST ENANTIOSELECTIVE FLUORINATION REACTION
DIFFERDING, E
LANG, RW
[J]. TETRAHEDRON LETTERS, 1988, 29 (47) : 6087 - 6090
[8] An efficient enantioselective fluorination of various β-ketoesters catalyzed chiral palladium complexes
Hamashima, Y
Yagi, K
Takano, H
Tamás, L
Sodeoka, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) : 14530 - 14531
[9] Hintermann L, 2000, ANGEW CHEM INT EDIT, V39, P4359, DOI 10.1002/1521-3773(20001201)39:23<4359::AID-ANIE4359>3.0.CO
[10] 2-P

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