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

[51] Shiro M., 2008, ANGEW CHEM, V120, P4225
[52] Mechanism of N-Fluorobenzenesulfonimide Promoted Diamination and Carboamination Reactions: Divergent Reactivity of a Pd(IV) Species
Sibbald, Paul A.
Rosewall, Carolyn F.
Swartz, Rodney D.
Michael, Forrest E.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) : 15945 - 15951
[53] Palladium-Catalyzed Diamination of Unactivated Alkenes Using N-Fluorobenzenesulfonimide as Source of Electrophilic Nitrogen
Sibbald, Paul A.
Michael, Forrest E.
[J]. ORGANIC LETTERS, 2009, 11 (05) : 1147 - 1149
[54] Recent highlights in electrophilic fluorination with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Singh, RP
Shreeve, JM
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (01) : 31 - 44
[55] Palladium-Catalyzed C-H Aminations of Anilides with N-Fluorobenzenesulfonimide
Sun, Kai
Li, Yan
Xiong, Tao
Zhang, Jingping
Zhang, Qian
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) : 1694 - 1697
[56] 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
[57] Takeuchi Y, 1997, CHEM PHARM BULL, V45, P1085
[58] BINBAM - A New Motif for Strong and Chiral Bronsted Acids
Treskow, Marcel
Neudoerfl, Joerg
Giernoth, Ralf
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (22) : 3693 - 3697
[59] Wang L., 2011, ANGEW CHEM, V123, P9614
[60] The Long-Arm Effect: Influence of Axially Chiral Phosphoramidite Ligands on the Diastereo- and Enantioselectivity of the Tandem 1,4-Addition/Fluorination
Wang, Lian
Meng, Wei
Zhu, Chuan-Le
Zhen, Yan
Nie, Jing
Ma, Jun-An
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) : 9442 - 9446

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