Rhodium(II) catalysed three-component coupling: a novel reaction of in situ generated iodonium ylides

被引：9

作者：

Bonge, Hanne Therese ^{[1
]}

Hansen, Tore ^{[1
]}

机构：

[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 01期

关键词：

D O I：

10.1016/j.tetlet.2007.11.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic ethers are cleaved in the presence of nitromethane, a base, a hypervalent iodine compound and a Rh(II) catalyst to give nitromethoxy acetates in up to 71% isolated yields. The reaction is a three-component coupling of an ether with a nitromethane derived carbenoid and a carboxylate group originating from the hypervalent iodine compound. (C) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：57 / 61

页数：5

相关论文

共 18 条

[1]

Antkowiak WZ, 2001, POL J CHEM, V75, P875

[2] RhII-catalyzed cycloadditions of carbomethoxy iodonium ylides [J].

Batsila, C ;

Kostakis, G ;

Hadjiarapoglou, LP .

TETRAHEDRON LETTERS, 2002, 43 (34) :5997-6000

[3] Cyclopropanation of alkenes using hypervalent iodine reagents [J].

Biland, AS ;

Altermann, S ;

Wirth, T .

ARKIVOC, 2003, :164-169

[4] Cyclopropanation of olefins with nitromethane [J].

Bonge, Hanne Therese ;

Hansen, Tore .

SYNLETT, 2007, (01) :55-58

[5]

CLARK JS, 2002, NITROGEN OXYGEN SULF, V13

[6] 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

[7] Rhodium(II)-catalyzed inter- and intramolecular cyclopropanations with diazo compounds and phenyliodonium ylides: Synthesis and chiral analysis [J].

Ghanem, A ;

Lacrampe, F ;

Schurig, V .

HELVETICA CHIMICA ACTA, 2005, 88 (02) :216-239

[8] One-pot synthesis and chiral analysis of cyclopropane derivatives [J].

Ghanem, A ;

Aboul-Enein, HY ;

Müller, P .

CHIRALITY, 2005, 17 (01) :44-50

[9]

Lin SJ, 1997, HETEROCYCLES, V45, P1879

[10] Expedient synthesis of cyclopropane α-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate [J].

Moreau, B ;

Charette, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18014-18015