Synthesis of Oxazolidin-2-ones via a Copper(I)-Catalyzed Tandem Decarboxylative/Carboxylative Cyclization of a Propiolic Acid, a Primary Amine and an Aldehyde

被引：53

作者：

Feng, Huangdi ^{[1
,2
]}

Ermolat'ev, Denis S. ^{[1
]}

Song, Gonghua ^{[2
]}

Van der Eycken, Erik V. ^{[1
]}

机构：

[1] Katholieke Univ Leuven, LOMAC, Dept Chem, Celestijnenlaan 200F, B-3001 Louvain, Belgium

[2] E China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 2-3期

关键词：

carboxylative cyclization; decarboxylative coupling; oxazolidinones; three-component coupling; CARBON-DIOXIDE; OXAZOLIDINONES; ALCOHOLS; CONSTRUCTION; DERIVATIVES; CATALYSIS; FIXATION; RING;

D O I：

10.1002/adsc.201100608

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A facile approach to polysubstituted oxazolidin-2-ones is presented via a copper(I)-catalyzed tandem decarboxylative/carboxylative cyclization of a propiolic acid, a primary amine and an aldehyde (PA2-coulpling). This new multicomponent coupling constitutes an efficient methodology to provide the corresponding oxazolidin-2-ones in good yields.

引用

页码：505 / 509

页数：5

共 55 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[2]

Ager DJ, 1997, ALDRICHIM ACTA, V30, P3

[3]

Alouane N., 2006, Synthesis, P860

[4] Catalysis research of relevance to carbon management: Progress, challenges, and opportunities [J].

Arakawa, H ;

Aresta, M ;

Armor, JN ;

Barteau, MA ;

Beckman, EJ ;

Bell, AT ;

Bercaw, JE ;

Creutz, C ;

Dinjus, E ;

Dixon, DA ;

Domen, K ;

DuBois, DL ;

Eckert, J ;

Fujita, E ;

Gibson, DH ;

Goddard, WA ;

Goodman, DW ;

Keller, J ;

Kubas, GJ ;

Kung, HH ;

Lyons, JE ;

Manzer, LE ;

Marks, TJ ;

Morokuma, K ;

Nicholas, KM ;

Periana, R ;

Que, L ;

Rostrup-Nielson, J ;

Sachtler, WMH ;

Schmidt, LD ;

Sen, A ;

Somorjai, GA ;

Stair, PC ;

Stults, BR ;

Tumas, W .

CHEMICAL REVIEWS, 2001, 101 (04) :953-996

[5] Developing innovative synthetic technologies of industria relevance based on carbon dioxide as raw material [J].

Aresta, M ;

Dibenedetto, A ;

Tommasi, I .

ENERGY & FUELS, 2001, 15 (02) :269-273

[6]

Barbachyn M.R., 2003, Angew. Chem, V115, P2056

[7] Oxazolidinone structure-activity relationships leading to linezolid [J].

Barbachyn, MR ;

Ford, CW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (18) :2010-2023

[8] Copper-Catalyzed Intramolecular C-H Amination [J].

Barman, Dipti N. ;

Nicholas, Kenneth M. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) :908-911

[9] Direct catalytic synthesis of enantiopure 5-substituted oxazolidinones from racemic terminal epoxides [J].

Bartoli, G ;

Bosco, M ;

Carlone, A ;

Locatelli, M ;

Melchiorre, P ;

Sambri, L .

ORGANIC LETTERS, 2005, 7 (10) :1983-1985

[10] An excellent procedure for the synthesis of oxazolidin-2-ones [J].

Bratulescu, George .

SYNTHESIS-STUTTGART, 2007, (20) :3111-3112

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