Catalytic enantioselective fluorination of oxindoles

被引：314

作者：

Hamashima, Y

Suzuki, T

Takano, H

Shimura, Y

Sodeoka, M ^{[1
]}

机构：

[1] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Miyagi 9808577, Japan

[2] JST, PRESTO, Wako, Saitama 3510198, Japan

[3] RIKEN, Wako, Saitama 3510198, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 29期

关键词：

D O I：

10.1021/ja0513077

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluorinated in a highly enantioselective manner (up to 96% ee). In addition, when R was a hydrogen atom, enantioselective fluorination followed by solvolysis gave a monofluorinated ester with up to 93% ee. To our knowledge, this is the first example of catalytic enantioselective fluorination of oxindoles. Copyright © 2005 American Chemical Society.

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页码：10164 / 10165

页数：2

相关论文

共 30 条

[1] Enantioselective organocatalytic α-fluorination of aldehydes [J].

Beeson, TD ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828

[2] Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids [J].

Bernardi, L ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2005, (10) :1324-1326

[3] DIASTEREOSELECTIVE FLUORINATION OF CHIRAL IMIDE ENOLATES USING N-FLUORO-O-BENZENEDISULFONIMIDE (NFOBS) [J].

DAVIS, FA ;

HAN, W .

TETRAHEDRON LETTERS, 1992, 33 (09) :1153-1156

[4] Direct organocatalytic α-fluorination of aldehydes and ketones [J].

Enders, D ;

Hüttl, MRM .

SYNLETT, 2005, (06) :991-993

[5]

Enders D, 2001, SYNTHESIS-STUTTGART, P2307

[6] Regio- and enantioselective synthesis of allylic fluorides by electrophilic fluorodesilylation of allyl silanes [J].

Greedy, B ;

Paris, JM ;

Vidal, T ;

Gouverneur, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (28) :3291-3294

[7] An efficient catalytic enantioselective fluorination of β-ketophosphonates using chiral palladium complexes [J].

Hamashima, Y ;

Suzuki, T ;

Shimura, Y ;

Shimizu, T ;

Umebayashi, N ;

Tamura, T ;

Sasamoto, N ;

Sodeoka, M .

TETRAHEDRON LETTERS, 2005, 46 (09) :1447-1450

[8] Immobilization and reuse of Pd complexes in ionic liquid:: Efficient catalytic asymmetric fluorination and Michael reactions with β-ketoesters [J].

Hamashima, Y ;

Takano, H ;

Hotta, D ;

Sodeoka, M .

ORGANIC LETTERS, 2003, 5 (18) :3225-3228

[9] An efficient enantioselective fluorination of various β-ketoesters catalyzed chiral palladium complexes [J].

Hamashima, Y ;

Yagi, K ;

Takano, H ;

Tamás, L ;

Sodeoka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) :14530-14531

[10] Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: Catalytic enantioselective Michael reaction with enones [J].

Hamashima, Y ;

Hotta, D ;

Sodeoka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11240-11241