Cinchona Alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones

被引：135

作者：

Mizuta, Satoshi ^{[1
]}

Shibata, Norio ^{[1
]}

Akiti, Surendar ^{[1
]}

Fujimoto, Hiroyuki ^{[1
]}

Nakamura, Shuichi ^{[1
]}

Toru, Takeshi ^{[1
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 18期

关键词：

D O I：

10.1021/ol701791r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic, nucleophilic enantioselective trifluoromethylation reaction of both acyclic and cyclic aryl ketones using the Ruppert-Prakash reagent is now at hand, with an operationally simple procedure, based on the combination of ammonium bromide of cinchona alkaloids with TMAF. The procedure is reliable and general. Trifluoromethyl-substituted tetrasubstituted aryl alcohols have been synthesized in up to 94% ee.

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页码：3707 / 3710

页数：4

相关论文

共 43 条

[1] CHIRAL QUARTERNARY AMMONIUM FLUORIDE - A NEW REAGENT FOR CATALYTIC ASYMMETRIC ALDOL REACTIONS [J].

ANDO, A ;

MIURA, T ;

TATEMATSU, T ;

SHIORI, T .

TETRAHEDRON LETTERS, 1993, 34 (09) :1507-1510

[2]

BILDER DM, 2002, Patent No. 2002078628

[3] How to reach stereogenic trifluoromethylated carbon? En route to the "grail" of the asymmetric trifluoromethylation reaction [J].

Billard, Thierry ;

Langlois, Bernard R. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (06) :891-897

[4]

Caron S, 2003, SYNTHESIS-STUTTGART, P1693

[5]

DEGRAFFENREID MR, 2002, Patent No. 2005063247

[6] Fluorobis(phenylsulfonyl)methane: A fluoromethide equivalent and palladium-catalyzed enantioselective allylic monofluoromethylation [J].

Fukuzumi, Takeo ;

Shibata, Norio ;

Sugiura, Masayoshi ;

Yasui, Hiroyuki ;

Nakamura, Shuichi ;

Toru, Takeshi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) :4973-4977

[7] Lewis base catalyzed trifluoromethylation of carbonyl compounds with trialkyl(trifluoromethyl)silanes [J].

Hagiwara, T ;

Kobayashi, T ;

Fuchikami, T .

MAIN GROUP CHEMISTRY, 1997, 2 (01) :13-15

[8] Enantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalyst [J].

Horikawa, M ;

Busch-Petersen, J ;

Corey, EJ .

TETRAHEDRON LETTERS, 1999, 40 (20) :3843-3846

[9]

ISEKI K, 1995, REV HETEROATOM CHEM, V12, P211

[10] ASYMMETRIC TRIFLUOROMETHYLATION OF ALDEHYDES AND KETONES WITH TRIFLUOROMETHYLTRIMETHYSILANE CATALYZED BY CHIRAL QUATERNARY AMMONIUM FLUORIDES [J].

ISEKI, K ;

NAGAI, T ;

KOBAYASHI, Y .

TETRAHEDRON LETTERS, 1994, 35 (19) :3137-3138

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