Iron-catalyzed aziridination reactions

被引：108

作者：

Nakanishi, Masafumi ^{[1
]}

Salit, Anne-Frederique ^{[1
]}

Bolm, Carsten ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 11-12期

关键词：

asymmetric catalysis; aziridination; iron; nitrogen transfer; sulfonamides;

D O I：

10.1002/adsc.200700519

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A small quantity of iron(II) triflate (2.5 to 5 mol%) catalyzes the aziridination reactions of enol silyl ethers with tosylimino(iodo)benzenw (PhINTs) in acetonitrile to give alpha-N-tosylamido ketones by subsequent aziridine ring opening. Olefins are converted into aziridines by 5 mol% of this catalyst system. Both reactions afford the corresponding products in moderate to good yields. In the presence of chiral ligands asymmetric aziridinations have been achieved.

引用

页码：1835 / 1840

页数：6

共 82 条

[1]

Adam W, 2000, EUR J ORG CHEM, V2000, P557

[2] Catalytic aziridination of olefins and amidation of thioanisole by a non-heme iron complex [J].

Avenier, F ;

Latour, JM .

CHEMICAL COMMUNICATIONS, 2004, (13) :1544-1545

[3] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[4] Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate [J].

Catino, AJ ;

Nichols, JM ;

Forslund, RE ;

Doyle, MP .

ORGANIC LETTERS, 2005, 7 (13) :2787-2790

[5] Catalytic aziridination of styrene with copper complexes of substituted 3,7-diazabicyclo[3.3.1]nonanones [J].

Comba, P ;

Merz, M ;

Pritzkow, H .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2003, (09) :1711-1718

[6] Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes [J].

Correa, Arkaitz ;

Mancheno, Olga Garcia ;

Bolm, Carsten .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (06) :1108-1117

[7] Efficient aziridination of olefins catalyzed by a unique disilver(I) compound [J].

Cui, Y ;

He, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) :16202-16203

[8] Iminoiodanes and C-N bond formation in organic synthesis [J].

Dauban, P ;

Dodd, RH .

SYNLETT, 2003, (11) :1571-1586

[9] PhI=NSes: A new iminoiodinane reagent for the copper-catalyzed aziridination of olefins [J].

Dauban, P ;

Dodd, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5304-5307

[10] Copper-catalyzed nitrogen transfer mediated by iodosylbenzene PhI=O [J].

Dauban, P ;

Sanière, L ;

Tarrade, A ;

Dodd, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) :7707-7708

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