Platinum(II)/europium(III)-catalyzed intramolecular hydroalkylation of 4-pentenyl β-dicarbonyl compounds

被引:23
作者
Liu, C [1 ]
Widenhoefer, RA [1 ]
机构
[1] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/j.tetlet.2004.11.060
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of 5,5-dimethyl-8-nonene-2,4-dione with a catalytic mixture of (PtCL2(CH2=CH2)](2) (2) (1 mol%). and EuCl3, (2 mol%) in dioxane that contained HC1 (l.0equiv) at 90degreesC for 18h led to the isolation of 2-acetyl-3.6.6-trimethyl-2 -cyclohexanone in 85% yield. A number of 4-pentenyl beta-dicarbonyl compounds underwent intramolecular hydroalkylation to form Cyclohexanones in moderate to excellent yield. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:285 / 287
页数:3
相关论文
共 19 条
[1]   LANTHANIDES IN ORGANIC-SYNTHESIS - EU+3-CATALYZED MICHAEL ADDITION OF 1,3-DICARBONYL COMPOUNDS [J].
BONADIES, F ;
LATTANZI, A ;
ORELLI, LR ;
PESCI, S ;
SCETTRI, A .
TETRAHEDRON LETTERS, 1993, 34 (47) :7649-7650
[2]   OLEFIN CO-ORDINATION COMPOUNDS .4. DIENE COMPLEXES OF PLATINUM(II) - THE STRUCTURE OF HOFMANN AND VON NARBUTTS [DICYCLOPENTADIENE(RO)PTCL] [J].
CHATT, J ;
VALLARINO, LM ;
VENANZI, LM .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (JUN) :2496-2505
[3]   QUANTITATIVE-EVALUATION OF STERIC EFFECTS IN SN2 RING-CLOSURE REACTIONS [J].
DETAR, DF ;
LUTHRA, NP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (13) :4505-4512
[4]   IRREVERSIBLE ADDITION OF CARBON NUCLEOPHILES TO ETHYLENE IN CATIONIC PLATINUM(II) COMPLEXES [J].
FANIZZI, FP ;
INTINI, FP ;
MARESCA, L ;
NATILE, G .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (02) :309-312
[5]   Compounds of platinum chloride with di-cyclopentadiene. [J].
Hofmann, KA ;
von Narbutt, J .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1908, 41 :1625-1628
[6]   Ytterbium triflate catalyzed Michael additions of beta-ketoesters in water [J].
Keller, E ;
Feringa, BL .
TETRAHEDRON LETTERS, 1996, 37 (11) :1879-1882
[7]   Platinum-catalyzed intramolecular alkylation of indoles with unactivated olefins [J].
Liu, C ;
Han, XQ ;
Wang, X ;
Widenhoefer, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3700-3701
[8]   NICKEL-CATALYZED MICHAEL ADDITIONS OF BETA-DICARBONYLS [J].
NELSON, JH ;
HOWELLS, PN ;
DELULLO, GC ;
LANDEN, GL ;
HENRY, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (07) :1246-1249
[9]   ADDITION REACTIONS ON COORDINATED OLEFINIC LIGANDS .I. REACTIONS OF AMINES WITH DIENE COMPLEXES OF PLATINUM(2) AND PALLADIUM(2) [J].
PALUMBO, R ;
DERENZI, A ;
PANUNZI, A ;
PAIARO, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (14) :3874-&
[10]   Palladium-catalyzed intramolecular oxidative alkylation of unactivated olefins [J].
Pei, T ;
Wang, X ;
Widenhoefer, FA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (03) :648-649