Mild and efficient one-pot synthesis of chiral β-chalcogen amides via 2-oxazoline ring-opening reaction mediated by indium metal

被引：18

作者：

Braga, Antonio L. ^{[1
]}

Galetto, Fabio Z. ^{[1
]}

Taube, Paulo S. ^{[1
]}

Paixao, Marcio W. ^{[1
,2
]}

Silveira, Claudio C. ^{[1
]}

Singh, Devender ^{[1
]}

Vargas, Fabricio ^{[1
,2
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

[2] Univ Sao Paulo, Inst Quim, BR-05508900 Sao Paulo, Brazil

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2008年 / 693卷 / 24期

关键词：

beta-Chalcogen amides; 2-Oxazolines; Ring-opening reaction; Indium metal;

D O I：

10.1016/j.jorganchem.2008.08.031

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple and efficient procedure for the synthesis of beta-seleno and beta-thio amides via the ring-opening reaction of chiral 2-oxazolines in the presence of indium metal has been developed. Features of this method include the following: (i) easily and accessible starting materials; (ii) indium metal is more stable and less expensive then its respective salts; (iii) useful to excellent yields of beta-chalcogen amides derivatives. (C) 2008 Elsevier B. V. All rights reserved.

引用

页码：3563 / 3566

页数：4

共 64 条

[1] Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands [J].

Anderson, JC ;

Cubbon, R ;

Harding, M ;

James, DS .

TETRAHEDRON-ASYMMETRY, 1998, 9 (19) :3461-3490

[2] Synthesis of novel Se-substituted selenocysteine derivatives as potential kidney selective prodrugs of biologically active selenol compounds: Evaluation of kinetics of beta-elimination reactions in rat renal cytosol [J].

Andreadou, I ;

Menge, WMPB ;

Commandeur, JNM ;

Worthington, EA ;

Vermeulen, NPE .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (10) :2040-2046

[3]

Balzani V, 2000, ANGEW CHEM INT EDIT, V39, P3348, DOI 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO

[4]

2-X

[5] Indium(I) iodide-mediated regioselective ring opening of epoxides with diphenyldiselenide:: The preparation of β-hydroxy selenides [J].

Barros, OSD ;

de Carvalho, AB ;

Lang, ES ;

Peppe, C .

LETTERS IN ORGANIC CHEMISTRY, 2004, 1 (01) :43-46

[6]

Barros OSD, 2002, TETRAHEDRON LETT, V43, P7921

[7] A convenient synthesis of some symmetrical and unsymmetrical diarylmethyl sulfur and selenium compounds:: X-ray crystal structure of diphenylmethylseleno-2-propene and bis[p-chlorophenyl(phenyl)methyl] diselenide [J].

Bhasin, KK ;

Singh, N ;

Kumar, R ;

Deepali, DG ;

Mehta, SK ;

Klapoetke, TM ;

Crawford, MJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (21) :3327-3334

[8] Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes [J].

Braga, AL ;

Paixao, MW ;

LUdtke, DS ;

Silveira, CC ;

Rodrigues, OED .

ORGANIC LETTERS, 2003, 5 (15) :2635-2638

[9] The facile synthesis of chiral oxazoline catalysts for the diethylzinc addition to aldehydes [J].

Braga, AL ;

Rubim, RM ;

Schrekker, HS ;

Wessjohann, LA ;

de Bolster, MWG ;

Zeni, G ;

Sehnem, JA .

TETRAHEDRON-ASYMMETRY, 2003, 14 (21) :3291-3295

[10] Modular chiral selenium-containing oxazolines:: synthesis and application in the palladium-catalyzed asymmetric allylic alkylation [J].

Braga, AL ;

Lüdtke, DS ;

Sehnem, JA ;

Alberto, EE .

TETRAHEDRON, 2005, 61 (49) :11664-11671

← 1 2 3 4 5 6 7 →