Cyclopropanation of olefins with nitromethane

被引:17
作者
Bonge, Hanne Therese [1 ]
Hansen, Tore [1 ]
机构
[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway
关键词
cyclopropanation; iodonium ylides; rhodium; nitrocyclopropanes; nitrodiazomethane;
D O I
10.1055/s-2006-958437
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A procedure for the use of nitromethane as an iodonium ylide precursor has been developed. Electron-rich olefins are cyclopropanated with nitromethane in the presence of bis(acetoxy)iodobenzene, a base and a Rh(II) catalyst to provide nitrocyclopropanes in moderate to good yields.
引用
收藏
页码:55 / 58
页数:4
相关论文
共 13 条
[1]   Synthesis of α-nitro-α-diazocarbonyl derivatives and their applications in the cyclopropanation of alkenes and in O-H insertion reactions [J].
Charette, AB ;
Wurz, RP ;
Ollevier, T .
HELVETICA CHIMICA ACTA, 2002, 85 (12) :4468-4484
[2]   Trifluoromethanesulfonyl azide:: A powerful reagent for the preparation of α-nitro-α-diazocarbonyl derivatives [J].
Charette, AB ;
Wurz, RP ;
Ollevier, T .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9252-9254
[3]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[4]   DIRHODIUM(II) TETRAKIS(CARBOXAMIDATES) WITH CHIRAL LIGANDS - STRUCTURE AND SELECTIVITY IN CATALYTIC METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP ;
WINCHESTER, WR ;
HOORN, JAA ;
LYNCH, V ;
SIMONSEN, SH ;
GHOSH, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :9968-9978
[5]   Expanding the scope of C-H amination through catalyst design [J].
Espino, CG ;
Fiori, KW ;
Kim, M ;
Du Bois, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) :15378-15379
[6]  
Feuer H., 1990, In Nitro Compounds: Recent Advances in Synthesis and Chemistry
[7]  
Georgakopoulou G, 2001, SYNLETT, P1843
[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]   Rh(II)-catalyzed enantioselective cyclopropanation of olefins with dimethyl malonate via in situ generated phenyliodonium ylide [J].
Muller, P ;
Ghanem, A .
ORGANIC LETTERS, 2004, 6 (23) :4347-4350
[10]   Asymmetric cyclopropanation of olefins with an in situ generated phenyliodonium ylide [J].
Müller, P ;
Ghanem, A .
SYNLETT, 2003, (12) :1830-1833