Highly Wolff selective Rh(II) catalysed decomposition of α-diazo-β-ketophosphonates having an oxygen atom adjacent to γ-position

被引：5
作者：
Boukraa, M
Dayoub, W
Doutheau, A
机构：
[1] Inst Natl Sci Appl, UMR CNRS 5181, Chim Organ Lab, F-69621 Villeurbanne, France
[2] Fac Sci Tunis, Mat Lab, Tunis 1060, Tunisia
来源：
LETTERS IN ORGANIC CHEMISTRY | 2006年 / 3卷 / 03期
关键词：
alpha-diazo-beta-keto-com pounds; rhodiocarbenoid; Wolff rearrangement; ketenes;
D O I：
10.2174/157017806775789877
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
alpha-Diazo-beta-ketophosphonates, bearing an oxygen atom adjacent to the gamma position, led mainly or exclusively to compounds derived from a Wolff rearrangement when submitted to the action of a catalytic amount of Rh(II) in refluxing toluene. It is suggested that the presence of this inductive withdrawing electronic atom prevents competing intramolecular C-H insertion reactions to occur.
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收藏
页码：204 / 206
页数：3
相关论文
共 14 条
[1]   RHODIUM ACETATE CATALYZES THE ADDITION OF CARBENOIDS ALPHA-OXYGENS TO ETHER OXYGENS [J].
ADAMS, J ;
POUPART, MA ;
GRENIER, L ;
SCHALLER, C ;
OUIMET, N ;
FRENETTE, R .
TETRAHEDRON LETTERS, 1989, 30 (14) :1749-1752
[2]   Synthesis and enzyme-catalysed reductions of 2-oxo acids with oxygen containing side-chains [J].
Bhalay, G ;
Clough, S ;
McLaren, L ;
Sutherland, A ;
Willis, CL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (06) :901-910
[3]   Anomalous products from intramolecular insertion reactions of rhodium carbenoids into the alpha-C-H bonds of ethers [J].
Clark, JS ;
Dossetter, AG ;
Russell, CA ;
Whittingham, WG .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (15) :4910-4911
[4]   Chemoselectivity in the rhodium(II) acetate catalysed decomposition of alpha-diazo-beta-keto-gamma,delta-alkenyl-delta-aryl compounds: Aromatic C-H insertion reaction or Wolff rearrangement-electrocyclization [J].
Collomb, D ;
Chantegrel, B ;
Deshayes, C .
TETRAHEDRON, 1996, 52 (31) :10455-10472
[5]   2-phosphonocyclopenten-2-ones from ε-tert-butyldimethylsilyloxy-α-diazo-β-ketophosphonates via a rhodium(II)-catalysed C-H insertion reaction [J].
Dayoub, W ;
Diab, Y ;
Doutheau, A .
TETRAHEDRON LETTERS, 2002, 43 (23) :4131-4132
[6]   α-phosphono-δ-lactones from γ-lactones via a rhodium(II)-catalysed Wolff rearrangement [J].
Dayoub, W ;
Diab, Y ;
Doutheau, A .
TETRAHEDRON LETTERS, 2001, 42 (48) :8455-8457
[7]  
Doyle M. P., 1998, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides
[8]   Stereocontrolled synthesis of the C(1)-C(11) subunit of the iejimalides [J].
Mendlik, MT ;
Cottard, M ;
Rein, T ;
Helquist, P .
TETRAHEDRON LETTERS, 1997, 38 (36) :6375-6378
[9]   A concise synthesis of the functionalised cyclopentane unit in the antitumoural antibiotic viridenomycin [J].
Pattenden, G ;
Blake, AJ ;
Constandinos, L .
TETRAHEDRON LETTERS, 2005, 46 (11) :1913-1915
[10]  
POJER PM, 1976, TETRAHEDRON LETT, V35, P3067
12