Chiral N-Fluorodibenzenesulfonimide Analogues for Enantioselective Electrophilic Fluorination and Oxidative Fluorination

被引：34

作者：

Zhu, Chuan-Le ^{[1
,2
,3
]}

Maeno, Mayaka ^{[4
]}

Zhang, Fa-Guang ^{[3
]}

Shigehiro, Taiki ^{[5
]}

Kagawa, Takumi ^{[5
]}

Kawada, Kosuke ^{[5
]}

Shibata, Norio ^{[4
]}

Ma, Jun-An ^{[3
]}

Cahard, Dominique ^{[1
,2
]}

机构：

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

[2] INSA Rouen, F-76821 Mont St Aignan, France

[3] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China

[4] Nagoya Inst Technol, Dept Nanopharmaceut Sci, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

[5] TOSOH F TECH Inc, Res Lab, Yamaguchi 7460006, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 29期

基金：

中国国家自然科学基金;

关键词：

Chirality; Enantioselectivity; Fluorine; Oxidation; PALLADIUM-CATALYZED DIAMINATION; ASYMMETRIC FLUORINATION; CINCHONA ALKALOIDS; FLUOROAMMONIUM SALTS; COMBINATIONS; ALKENES; AGENTS; SELECTFLUOR; 1,1-DIOXIDE; REAGENTS;

D O I：

10.1002/ejoc.201300956

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This work describes the design, synthesis, and application of de novo chiral fluorinating agents as analogues of popular N-fluorodibenzenesulfonimide (NFSI). The fluorination step by means of elemental fluorine is presented. Enantioselective fluorination is demonstrated in cyclic -keto esters and in the synthesis of BMS-204352 (up to 86%ee). Oxidative aminofluorination is also examined.

引用

页码：6501 / 6505

页数：5

共 65 条

[1] [Anonymous], ANGEW CHEM
[2] Nucleophilic reactivity towards electrophilic fluorinating agents:: reaction with N-fluorobenzenesulfonimide ((PhSO2)2NF)
Antelo, JM
Crugeiras, J
Leis, JR
Ríos, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (10): : 2071 - 2076
[3] Badoux J., 2007, ORG REACT, V69, P347
[4] Enantioselective electrophilic fluorination: a study of the fluorine-transfer from achiral N-F reagents to cinchona alkaloids
Baudequin, C
Loubassou, JF
Plaquevent, JC
Cahard, D
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2003, 122 (02) : 189 - 193
[5] Enantioselective electrophilic fluorination in ionic liquids
Baudequin, C
Plaquevent, JC
Audouard, C
Cahard, D
[J]. GREEN CHEMISTRY, 2002, 4 (06) : 584 - 586
[6] N-Fluorobenzenesulfonimide
Bizet, Vincent
[J]. SYNLETT, 2012, (18) : 2719 - 2720
[7] 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
[8] 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
[9] 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
[10] Desmurs J.-R., 2001, Patent No. 2001090107

← 1 2 3 4 5 6 7 →