Selective oxidation of alkenes and alkynes catalyzed by copper complexes

被引：40

作者：

Alvarez, Leonardo X. ^{[1
]}

Christ, M. Lorraine ^{[1
]}

Sorokin, Alexander B. ^{[1
]}

机构：

[1] Inst Rech Catalyse, F-69626 Villeurbanne, France

来源：

APPLIED CATALYSIS A-GENERAL | 2007年 / 325卷 / 02期

关键词：

asymmetric oxidation; allylic oxidation; propargylic oxidation; copper catalysts; chiral bisoxazoline ligands;

D O I：

10.1016/j.apcata.2007.02.045

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Benzoic esters of 2-cyclohexen-1-ol and propargylic alcohols were prepared by direct selective copper-catalyzed allylic and propargylic oxidation of alkenes and alkynes, respectively, using t-butyl peroxybenzoate as the oxidant. The high olefin and acetylene conversions as well as the high product yields were obtained although enantioselectivity of this oxidation was moderate (e.e. < 68%). The reported optimized catalytic procedure is clean since the oxidation is carried out under mild conditions using stoichiometric amounts of oxidant and catalytic amounts of (CuOTf)(2)C6H6 in combination with bisoxazoline ligands. (c) 2007 Elsevier B.V. All rights reserved.

引用

收藏

页码：303 / 308

页数：6

相关论文

共 34 条

[1] Synthesis of novel C-nucleosides with potential applications in combinatorial and parallel synthesis [J].

Adlington, RM ;

Baldwin, JE ;

Pritchard, GJ ;

Spencer, KC .

TETRAHEDRON LETTERS, 2000, 41 (04) :575-578

[2] Copper catalyzed allylic oxidation with peresters [J].

Andrus, MB ;

Lashley, JC .

TETRAHEDRON, 2002, 58 (05) :845-866

[3] Highly enantioselective copper-bisoxazoline-catalyzed allylic oxidation of cyclic olefins with tert-butyl p-nitroperbenzoate [J].

Andrus, MB ;

Zhou, ZN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) :8806-8807

[4] THE ASYMMETRIC KHARASCH REACTION - CATALYTIC ENANTIOSELECTIVE ALLYLIC ACYLOXYLATION OF OLEFINS WITH CHIRAL COPPER(I) COMPLEXES AND TERT-BUTYL PERBENZOATE [J].

ANDRUS, MB ;

ARGADE, AB ;

CHEN, X ;

PAMMENT, MG .

TETRAHEDRON LETTERS, 1995, 36 (17) :2945-2948

[5] Catalytic enantioselective allylic oxidation of olefins with copper(I) catalysts and new perester oxidants [J].

Andrus, MB ;

Chen, X .

TETRAHEDRON, 1997, 53 (48) :16229-16240

[6] Asymmetric allylic oxidation with biarylbisoxazoline-copper(I) catalysis [J].

Andrus, MB ;

Asgari, D .

TETRAHEDRON, 2000, 56 (32) :5775-5780

[7] Enantiopure fluorous bis(oxazolines): Synthesis and applications in catalytic asymmetric reactions [J].

Bayardon, J ;

Sinou, D .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3121-3128

[8] Tuneable asymmetric copper-catalysed allylic amination and oxidation reactions [J].

Clark, JS ;

Roche, C .

CHEMICAL COMMUNICATIONS, 2005, (41) :5175-5177

[9] Asymmetric allyfic oxidation of bridged-bicyclic alkenes using a copper-catalysed symmetrising-desymmetrising Kharasch-Sosnovsky reaction [J].

Clark, JS ;

Clarke, MR ;

Clough, J ;

Blake, AJ ;

Wilson, C .

TETRAHEDRON LETTERS, 2004, 45 (51) :9447-9450

[10] Enantioselective allylic acyloxylation catalysed by copper-oxazoline complexes [J].

Clark, JS ;

Tolhurst, KF ;

Taylor, M ;

Swallow, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (07) :1167-1169

← 1 2 3 4 →