Remarkably efficient olefin aziridination mediated by a new copper(II) complex

被引：55

作者：

Halfen, JA ^{[1
]}

Hallman, JK ^{[1
]}

Schultz, JA ^{[1
]}

Emerson, JP ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Eau Claire, WI 54702 USA

来源：

ORGANOMETALLICS | 1999年 / 18卷 / 26期

关键词：

D O I：

10.1021/om9908579

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The structurally characterized copper complex [(i-Pr(3)TACN)Cu(O2CCF3)(2)] (1) mediates nitrene transfer from PhINTs to olefins to form N-tosylaziridines in good to excellent yields, in catalytic amounts (0.5 mol %) 1 order of magnitude less than is required for other copper catalysts, such as [Cu(acac)(2)]. Nitrene transfer reactivity has also been observed with substituted styrenes, internal and terminal aliphatic olefins, and sulfides, suggesting that 1 may be a general nitrene transfer catalyst for use on organic synthesis.

引用

页码：5435 / 5437

页数：3

共 27 条

[1] Catalytic asymmetric aziridination with a chiral VAPOL-boron Lewis acid
Antilla, JC
Wulff, WD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 5099 - 5100
[2] Lewis acid-catalyzed synthesis of aziridines
Casarrubios, L
Perez, JA
Brookhart, M
Templeton, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) : 8358 - 8359
[3] Stereocontrolled synthesis of the fully elaborated aziridine core of the azinomycins
Coleman, RS
Kong, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (14) : 3538 - 3539
[4] Substituent effects on the reaction rates of copper-catalyzed cyclopropanation and aziridination of para-substituted styrenes
Díaz-Requejo, MM
Perez, PJ
Brookhart, M
Templeton, JL
[J]. ORGANOMETALLICS, 1997, 16 (20) : 4399 - 4402
[5] BIS(OXAZOLINE) COPPER-COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS
EVANS, DA
FAUL, MM
BILODEAU, MT
ANDERSON, BA
BARNES, DM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5328 - 5329
[6] COPPER-CATALYZED AZIRIDINATION OF OLEFINS BY (N-(PARA-TOLUENESULFONYL)IMINO)PHENYLIODINANE
EVANS, DA
FAUL, MM
BILODEAU, MT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) : 6744 - 6746
[7] EVANS DA, 1994, J AM CHEM SOC, V116, P2742
[8] PRACTICAL TOTAL SYNTHESIS OF (+/-)-MITOMYCIN-C
FUKUYAMA, T
YANG, LH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) : 8303 - 8304
[9] SYNTHETIC MODEL OF THE SUBSTRATE ADDUCT TO THE REDUCED ACTIVE-SITE OF COPPER NITRITE REDUCTASE
HALFEN, JA
TOLMAN, WB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) : 5475 - 5476
[10] CARBENOID TRANSFER TO IMINES - A NEW ASYMMETRIC CATALYTIC SYNTHESIS OF AZIRIDINES
HANSEN, KB
FINNEY, NS
JACOBSEN, EN
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (06) : 676 - 678

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