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

被引：168

作者：

Cahard, D

Audouard, C

Plaquevent, JC

Roques, N

机构：

[1] Univ Rouen, IRCOF, UPRESA 6014, F-76821 Mt St Aignan, France

[2] Rhodia Rech, F-69192 St Fons, France

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 23期

关键词：

D O I：

10.1021/ol006610l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The first enantiopure N-fluoro quaternary ammonium salts of cinchona alkaloids as enantioselective fluorinating agents are reported. A one step transfer-fluorination on the naturally occurring cinchona alkaloids gave the fluorinating agents F-CA BF4. This new generation of fluorinating agents exhibited asymmetric induction up to 61% on fluorination of enolates and silyl enol ethers of 2-methyl-1-tetralone.

引用

页码：3699 / 3701

页数：3

共 8 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] Synthesis of α-fluoro aldehydes and ketones.: A review
Davis, FA
Kasu, PVN
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1999, 31 (02) : 125 - 143
[3] 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
[4] 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
[5] NEW FLUORINATING REAGENTS .1. THE 1ST ENANTIOSELECTIVE FLUORINATION REACTION
DIFFERDING, E
LANG, RW
[J]. TETRAHEDRON LETTERS, 1988, 29 (47) : 6087 - 6090
[6] Soloshonok V. A., 1999, ENANTIOCONTROLLED SY
[7] N-fluoro-3-cyclohexyl-3-methyl-2,3-dihydrobenzo[1,2-d]isothiazole 1,1-dioxide:: An efficient agent for electrophilic asymmetric fluorination of enolates
Takeuchi, Y
Suzuki, T
Satoh, A
Shiragami, T
Shibata, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) : 5708 - 5711
[8] Takeuchi Y, 1997, CHEM PHARM BULL, V45, P1085

← 1 →