Reactivities and selectivities in macrocyclic addition reactions with diazoacetates using copper(I) and rhodium(II) catalysts

被引:27
作者
Doyle, MP [1 ]
Hu, WH [1 ]
机构
[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(00)01075-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactions of diazoacetates linked through three ethylene glycol units to allyl, methallyl, propargyl, or furfuryl, catalyzed by copper(I) and rhodium(II) compounds, are investigated for chemoselectivity, diastereoselectivity, and enantioselectivity. The most reactive catalysts show the highest preference for addition over carbon-hydrogen insertion. Addition is favored in the order: prapargyl > furfuyl > methallyl, allyl. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6265 / 6269
页数:5
相关论文
共 15 条
[1]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[2]   Recent advances in asymmetric catalytic metal carbene transformations [J].
Doyle, MP ;
Forbes, DC .
CHEMICAL REVIEWS, 1998, 98 (02) :911-935
[3]   Enantiocontrol in the generation and diastereoselective reactions of catalytically generated oxonium and iodonium ylides. Metal-stabilized ylides as reaction intermediates [J].
Doyle, MP ;
Forbes, DC ;
Vasbinder, MM ;
Peterson, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7653-7654
[4]   SYNTHESIS OF ALLENES BY [2,3]-SIGMATROPIC REARRANGEMENT OF PROP-2-YN-1-YL OXONIUM YLIDES FORMED IN RHODIUM(II) CARBOXYLATE CATALYZED-REACTIONS OF DIAZO-COMPOUNDS [J].
DOYLE, MP ;
BAGHERI, V ;
CLAXTON, EE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) :46-48
[5]   Catalytic intramolecular addition of metal carbenes to remote furans [J].
Doyle, MP ;
Chapman, BJ ;
Hu, WH ;
Peterson, CS ;
McKervey, MA ;
Garcia, CF .
ORGANIC LETTERS, 1999, 1 (09) :1327-1329
[6]   EXCEPTIONALLY HIGH TRANS (ANTI) STEREOSELECTIVITY IN CATALYTIC CYCLOPROPANATION REACTIONS [J].
DOYLE, MP ;
BAGHERI, V ;
WANDLESS, TJ ;
HARN, NK ;
BRINKER, DA ;
EAGLE, CT ;
LOH, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :1906-1912
[7]   Enantiocontrol in tandem carbonyl ylide formation and intermolecular 1,3-dipolar cycloaddition of α-diazo ketones mediated by chiral dirhodium(II) carboxylate catalyst [J].
Kitagaki, S ;
Anada, M ;
Kataoka, O ;
Matsuno, K ;
Umeda, C ;
Watanabe, N ;
Hashimoto, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (06) :1417-1418
[8]   ENANTIOSELECTIVE SYNTHESIS OF A 1,2-DISUBSTITUTED MITOSENE BY A COPPER-CATALYZED INTRAMOLECULAR CARBON-HYDROGEN INSERTION REACTION OF A DIAZO ESTER [J].
LIM, HJ ;
SULIKOWSKI, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2326-2327
[9]   Synthesis of the antitumor antibiotic FR-66979: Dmitrienko oxidative expansion of a fully functional core structure [J].
Lim, HJ ;
Sulikowski, GA .
TETRAHEDRON LETTERS, 1996, 37 (30) :5243-5246
[10]   ENANTIOSELECTIVITY AND DIASTEREOSELECTIVITY IN THE INTRAMOLECULAR CYCLOPROPANATION OF SECONDARY ALLYLIC DIAZOACETATES [J].
MARTIN, SF ;
SPALLER, MR ;
LIRAS, S ;
HARTMANN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4493-4494