Dimerization of cyclopropyl ketones and crossed reactions of cyclopropyl ketones with enones as an entry to five-membered rings

被引:116
作者
Liu, L
Montgomery, J [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[2] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
关键词
D O I
10.1021/ja0602187
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unexpected dimerization of cyclopropyl ketones was observed, and analysis of the reaction pathway led to development of a synthetically useful crossed reaction between cyclopropyl ketones and enones to afford densely functionalized cyclopentane products. Copyright © 2006 American Chemical Society.
引用
收藏
页码:5348 / 5349
页数:2
相关论文
共 22 条
[1]   LOW-COORDINATE CARBENE COMPLEXES OF NICKEL(0) AND PLATINUM(0) [J].
ARDUENGO, AJ ;
GAMPER, SF ;
CALABRESE, JC ;
DAVIDSON, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4391-4394
[2]  
BINGER P, 1987, TOP CURR CHEM, V135, P109
[3]   Nickel-catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes. A mild synthesis of substituted dihydrofurans [J].
Bowman, RK ;
Johnson, JS .
ORGANIC LETTERS, 2006, 8 (04) :573-576
[4]   Cyclic enolates of Ni and Pd:: Equilibrium between C- and O-bound tautomers and reactivity studies [J].
Cámpora, J ;
Maya, CM ;
Palma, P ;
Carmona, E ;
Gutiérrez, E ;
Ruiz, C ;
Graiff, C ;
Tiripicchio, A .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (23) :6889-6904
[5]   (TRIMETHYLSILYL)CYCLOPENTENE ANNULATION - A REGIOCONTROLLED APPROACH TO THE SYNTHESIS OF 5-MEMBERED RINGS [J].
DANHEISER, RL ;
CARINI, DJ ;
BASAK, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (06) :1604-1606
[6]   Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds [J].
Desai, LV ;
Hull, KL ;
Sanford, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9542-9543
[7]   A highly selective catalytic method for the oxidative functionalization of C-H bonds [J].
Dick, AR ;
Hull, KL ;
Sanford, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2300-2301
[8]  
Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO
[9]  
2-Y
[10]   Combined experimental and computational investigation of the mechanism of nickel-catalyzed three-component addition processes [J].
Hratchian, HP ;
Chowdhury, SK ;
Gutiérrez-García, VM ;
Amarasinghe, KKD ;
Heeg, MJ ;
Schlegel, HB ;
Montgomery, J .
ORGANOMETALLICS, 2004, 23 (20) :4636-4646