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

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