ω-Transaminases as efficient biocatalysts to obtain novel chiral selenium-amine ligands for Pd-catalysis

被引：31

作者：

Andrade, Leandro H. ^{[1
]}

Silva, Alexandre V. ^{[1
]}

Milani, Priscila ^{[1
]}

Koszelewski, Dominik ^{[2
]}

Kroutil, Wolfgang ^{[2
]}

机构：

[1] Univ Sao Paulo, Inst Chem, BR-05508900 Sao Paulo, Brazil

[2] Graz Univ, Dept Chem Organ & Bioorgan Chem, Res Ctr Appl Biocatalysis, Graz, Austria

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 09期

基金：

巴西圣保罗研究基金会;

关键词：

ASYMMETRIC-SYNTHESIS; DIFERROCENYL DICHALCOGENIDES; ORGANOSELENIUM COMPOUNDS; DONATING LIGANDS; DERIVATIVES; NITROGEN; AMIDES;

D O I：

10.1039/b920946h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

omega-Transaminases have been evaluated as biocatalysts in the reductive amination of organoselenium acetophenones to the corresponding amines, and in the kinetic resolution of racemic organoselenium amines. Kinetic resolution proved to be more efficient than the asymmetric reductive amination. By using these methodologies we were able to obtain both amine enantiomers in high enantiomeric excess (up to 99%). Derivatives of the obtained optically pure o-selenium 1-phenylethyl amine were evaluated as ligands in the palladium-catalyzed asymmetric alkylation, giving the alkylated product in up to 99% ee.

引用

页码：2043 / 2051

页数：9

共 42 条

[1] First chemoenzymatic synthesis of organoselenium amines and amides [J].

Andrade, Leandro H. ;

Silva, Alexandre V. .

TETRAHEDRON-ASYMMETRY, 2008, 19 (10) :1175-1181

[2] First dynamic kinetic resolution of selenium-containing chiral amines catalyzed by palladium (Pd/BaSO4) and Candida antartica lipase (CAL-B) [J].

Andrade, Leandro H. ;

Silva, Alexandre V. ;

Pedrozo, Eliane C. .

TETRAHEDRON LETTERS, 2009, 50 (30) :4331-4334

[3] Efficient synthesis of chiral β-seleno amides via ring-opening reaction of 2-oxazolines and their application in the palladium-catalyzed asymmetric allylic alkylation [J].

Braga, AL ;

Vargas, F ;

Sehnem, JA ;

Braga, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) :9021-9024

[4] Seleno-imine: A new class of versatile, modular N,Se ligands for asymmetric palladium-catalyzed allylic alkylation [J].

Braga, AL ;

Paixao, MW ;

Marin, G .

SYNLETT, 2005, (11) :1675-1678

[5]

BRAGA AL, 2008, SYNTHESIS-STUTTGART, P1262

[6] Enantioselective synthesis mediated by catalytic chiral organoselenium compounds [J].

Braga, Antonio L. ;

Ludtke, Diogo S. ;

Vargas, Fabricio .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (15) :1921-1938

[7] Catalytic applications of chiral organoselenium compounds in asymmetric synthesis [J].

Braga, Antonio L. ;

Ludtke, Diogo S. ;

Vargas, Fabricio ;

Braga, Rodolpho C. .

SYNLETT, 2006, (10) :1453-1466

[8] Microwave-mediated palladium-catalyzed asymmetric allylic alkylation using chiral β-seleno amides [J].

Braga, Antonio L. ;

Vargas, Fabricio ;

Sehnem, Jasquer A. ;

Wessjohann, Ludger A. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (22) :4993-4997

[9] New developments with chiral electrophilic selenium reagents [J].

Browne, Danielle M. ;

Wirth, Thomas .

CURRENT ORGANIC CHEMISTRY, 2006, 10 (15) :1893-1903

[10]

BUCHHOLZ S, 2007, BIOCATALYSIS PHARM B, P829

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