Mechanism of alkene aziridination in the [(biaryldiimine)CuI] catalyst system;: precise substrate orientation via two-centre binding

被引：84

作者：

Gillespie, KM ^{[1
]}

Crust, EJ ^{[1
]}

Deeth, RJ ^{[1
]}

Scott, P ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

来源：

CHEMICAL COMMUNICATIONS | 2001年 / 08期

关键词：

D O I：

10.1039/b101415n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The highly enantioselective (less than or equal to 98%) aziridination of cinnamate esters is achieved using the title catalyst system via a concerted non-polar mechanism involving ancillary binding of carbonyl group to copper.

引用

页码：785 / 786

页数：2

共 20 条

[1] Mechanistic studies of copper-catalyzed alkene aziridination [J].

Brandt, P ;

Södergren, MJ ;

Andersson, PG ;

Norrby, PO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :8013-8020

[2] Substituent effects on the reaction rates of copper-catalyzed cyclopropanation and aziridination of para-substituted styrenes [J].

Díaz-Requejo, MM ;

Perez, PJ ;

Brookhart, M ;

Templeton, JL .

ORGANOMETALLICS, 1997, 16 (20) :4399-4402

[3] FREE-RADICAL REACTIONS IN SOLUTION .7. SUBSTITUENT EFFECTS ON FREE-RADICAL REACTIONS - COMPARISON OF THE SIGMA-SCALE WITH OTHER MEASURES OF RADICAL STABILIZATION [J].

DINCTURK, S ;

JACKSON, RA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (08) :1127-1131

[4] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].

EVANS, DA ;

WOERPEL, KA ;

HINMAN, MM ;

FAUL, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728

[5] BIS(OXAZOLINE) AS LIGANDS FOR SELF-ASSEMBLING CHIRAL COORDINATION POLYMERS - STRUCTURE OF A COPPER(I) CATALYST FOR THE ENANTIOSELECTIVE CYCLOPROPANATION OF OLEFINS [J].

EVANS, DA ;

WOERPEL, KA ;

SCOTT, MJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (04) :430-432

[6] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS [J].

EVANS, DA ;

FAUL, MM ;

BILODEAU, MT ;

ANDERSON, BA ;

BARNES, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5328-5329

[7] COPPER-CATALYZED AZIRIDINATION OF OLEFINS BY (N-(PARA-TOLUENESULFONYL)IMINO)PHENYLIODINANE [J].

EVANS, DA ;

FAUL, MM ;

BILODEAU, MT .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6744-6746

[8]

EVANS DA, 1994, J AM CHEM SOC, V116, P2742

[9] Large-scale computational modeling of [Rh(DuPHOS)]+-catalyzed hydrogenation of prochiral enamides:: Reaction pathways and the origin of enantioselection [J].

Feldgus, S ;

Landis, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12714-12727

[10]

Harm AM, 1996, SYNLETT, P677

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