Rhodium(II)-carbenoid C-H insertion reactions in the synthesis of β-oxospirane systems

被引:17
作者
Aburel, PS [1 ]
Undheim, K [1 ]
机构
[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 12期
关键词
D O I
10.1039/b001988g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple one-pot procedure is described for the preparation of spiro[4.4]nonane-2,7-dione derivatives from open chain bis(alpha-diazoketones) by two consecutive intramolecular Rh(II)-catalyzed carbenoid insertion reactions. With 1-diazo-4-(3-oxocycloalkyl)butan-2-ones as substrates, the methodology provides 2,7-dioxospiranes with a cyclopentane ring spiroannulated onto a five-, six- or seven-membered cycloalkane.
引用
收藏
页码:1891 / 1896
页数:6
相关论文
共 26 条
[1]   Synthesis of spirosystems by rhodium(II)-carbenoid C-H insertion reactions. [J].
Aburel, PS ;
Undheim, K .
TETRAHEDRON LETTERS, 1998, 39 (22) :3813-3814
[2]   RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].
ADAMS, J ;
SPERO, DM .
TETRAHEDRON, 1991, 47 (10-11) :1765-1808
[3]   REDUCTIVE CYCLIZATION OF MERCURIAL ENONES [J].
DANISHEFSKY, S ;
CHACKALAMANNIL, S ;
UANG, BJ .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2231-2232
[4]  
Doyle M.P., 1998, MODERN CATALYTIC MET, P112
[5]  
DOYLE MP, 1995, COMPREHENSIVE ORGA 2, V12
[6]   PREPARATION OF BICYCLO[3.3.0]OCTANE-2,8-DIONE-DERIVATIVES AND DECALIN-1,8-DIONE-DERIVATIVES [J].
DUTHALER, RO ;
MAIENFISCH, P .
HELVETICA CHIMICA ACTA, 1984, 67 (03) :856-865
[7]  
FAHR E, 1960, LIEBIGS ANN CHEM, V638, P1
[8]   Palladium-mediated carbosubstitutions in spiranes [J].
Falck-Pedersen, ML ;
Romming, C ;
Undheim, K .
TETRAHEDRON, 1999, 55 (28) :8525-8538
[9]  
Fieser L.F., 1967, REAGENTS ORGANIC CHE, P191
[10]   HOMOENOLIC RADICAL DERIVED FROM PROPIONIC-ACID - A VERSATILE REAGENT FOR THE RADICAL VERSION OF THE MICHAEL REACTION [J].
FOUBELO, F ;
LLORET, F ;
YUS, M .
TETRAHEDRON, 1992, 48 (43) :9531-9536