A Simple Method for Asymmetric Trifluoromethylation of N-Acyl Oxazolidinones via Ru-Catalyzed Radical Addition to Zirconium Enolates

被引：113

作者：

Herrmann, Aaron T. ^{[1
]}

Smith, Lindsay L. ^{[1
]}

Zakarian, Armen ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 16期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION; CARBON BOND FORMATION; SOFT ENOLIZATION; DIASTEREOSELECTIVE TRIFLUOROMETHYLATION; PERFLUOROALKYLATION REACTIONS; MEDICINAL CHEMISTRY; TRIETHYLBORANE; FLUORINATION; ALDEHYDES; COMPLEX;

D O I：

10.1021/ja302552e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Ru-catalyzed direct thermal trifluoromethylation and perfluoroalkylation of N-acyloxazolidinones has been developed. The reaction is experimentally simple and requires inexpensive reagents while providing good yields of products with good levels of stereocontrol. Preliminary studies have shown notable compatibility with functional groups, aromatics, and certain heteroaromatic substituents. The described method provides a useful alternative for the synthesis of fluorinated materials in an experimentally convenient manner.

引用

页码：6976 / 6979

页数：4

共 42 条

[1] The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes
Allen, Anna E.
MacMillan, David W. C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) : 4986 - +
[2] Perhaloalkylation of Metal Enolates-Unconventional and Versatile
Amatov, Tynchtyk
Jahn, Ullrich
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (20) : 4542 - 4544
[3] Valence Tautomerism in Titanium Enolates: Catalytic Radical Haloalkylation and Application in the Total Synthesis of Neodysidenin
Beaumont, Stephane
Ilardi, Elizabeth A.
Monroe, Lucas R.
Zakarian, Armen
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1482 - +
[4] How to reach stereogenic trifluoromethylated carbon? En route to the "grail" of the asymmetric trifluoromethylation reaction
Billard, Thierry
Langlois, Bernard R.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (06) : 891 - 897
[5] Synthesis, characterization and biological evaluation of 7α-perfluoroalkylestradiol derivatives
Blazejewski, JC
Wilmshurst, MP
Popkin, MD
Wakselman, C
Laurent, G
Nonclercq, D
Cleeren, A
Ma, Y
Seo, HS
Leclercq, G
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (03) : 335 - 345
[6] 4-SUBSTITUTED-5,5-DIMETHYL OXAZOLIDIN-2-ONES AS EFFECTIVE CHIRAL AUXILIARIES FOR ENOLATE ALKYLATIONS AND MICHAEL ADDITIONS
DAVIES, SG
SANGANEE, HJ
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (03) : 671 - 674
[7] NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES
EVANS, DA
URPI, F
SOMERS, TC
CLARK, JS
BILODEAU, MT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) : 8215 - 8216
[8] ENANTIOSELECTIVE MICHAEL REACTIONS - DIASTEREOSELECTIVE REACTIONS OF CHLOROTITANIUM ENOLATES OF CHIRAL N-ACYLOXAZOLIDINONES WITH REPRESENTATIVE ELECTROPHILIC OLEFINS
EVANS, DA
BILODEAU, MT
SOMERS, TC
CLARDY, J
CHERRY, D
KATO, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) : 5750 - 5752
[9] FUCHIKAMI T, 1984, TETRAHEDRON LETT, V25, P303, DOI 10.1016/S0040-4039(00)99868-X
[10] Dual Ti-Ru Catalysis in the Direct Radical Haloalkylation of N-Acyl Oxazolidinones
Gu, Zhenhua
Herrmann, Aaron T.
Zakarian, Armen
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) : 7136 - 7139

← 1 2 3 4 5 →