Rh-catalyzed intermolecular reactions of alkynes with α-diazoesters that possess β-hydrogens:: Ligand-based control over divergent pathways

被引:143
作者
Panne, Patricia [1 ]
Fox, Joseph M. [1 ]
机构
[1] Univ Delaware, Dept Chem & Biochem, Brown Labs, Newark, DE 19716 USA
关键词
D O I
10.1021/ja0660195
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general method for Rh-catalyzed cyclopropenation is described, as is a Rh-catalyzed intermolecular alkyne insertion/Büchner ring expansion cascade. Ligand choice governs control over these divergent reaction pathways. Copyright © 2006 American Chemical Society.
引用
收藏
页码:22 / 23
页数:2
相关论文
共 33 条
[1]  
Baird M. S., 1996, CARBOCYCLIC 3 ME E A, V17, P2695
[2]   COMPETING O-H INSERTION AND BETA-ELIMINATION IN RHODIUM CARBENOID REACTIONS - SYNTHESIS OF 2-ALKOXY-3-ARYLPROPANOATES [J].
COX, GG ;
HAIGH, D ;
HINDLEY, RM ;
MILLER, DJ ;
MOODY, CJ .
TETRAHEDRON LETTERS, 1994, 35 (19) :3139-3142
[3]   Ring expansion-annulation strategy for the synthesis of substituted azulenes and oligoazulenes. 2. Synthesis of azulenyl halides, sulfonates, and azulenylmetal compounds and their application in transition-metal-mediated coupling reactions [J].
Crombie, AL ;
Kane, JL ;
Shea, KM ;
Danheiser, RL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) :8652-8667
[4]   Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].
Davies, HML ;
Beckwith, REJ .
CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903
[5]   Dirhodium(II) tetra(N-(dodecyl benzenesulfonyl)prolinate) catalyzed enantioselective cyclopropenation of alkynes [J].
Davies, HML ;
Lee, GH .
ORGANIC LETTERS, 2004, 6 (08) :1233-1236
[6]   A family of highly active copper(I)-homoscorpionate catalysts for the alkyne cyclopropenation reaction [J].
Díaz-Requejo, MM ;
Mairena, MA ;
Belderrain, TR ;
Nicasio, MC ;
Trofimenko, S ;
Pérez, PJ .
CHEMICAL COMMUNICATIONS, 2001, (18) :1804-1805
[7]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[8]  
Doyle MP, 2004, TOP ORGANOMETAL CHEM, V13, P203
[9]   EFFECTIVE USES OF DIRHODIUM(II) TETRAKIS[METHYL 2-OXOPYRROLIDINE-5(R OR S)-CARBOXYLATE] FOR HIGHLY ENANTIOSELECTIVE INTERMOLECULAR CYCLOPROPENATION REACTIONS [J].
DOYLE, MP ;
PROTOPOPOVA, M ;
MULLER, P ;
ENE, D ;
SHAPIRO, EA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8492-8498
[10]   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