AN IMPROVED PREPARATION OF DIPHENYLMETHYLENECYCLOPROPANES AND THEIR USE IN INTRAMOLECULAR PALLADIUM-CATALYZED [3+2] CYCLOADDITIONS

被引:29
作者
LEWIS, RT [1 ]
MOTHERWELL, WB [1 ]
SHIPMAN, M [1 ]
SLAWIN, AMZ [1 ]
WILLIAMS, DJ [1 ]
机构
[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED, DEPT CHEM, LONDON SW7 2AY, ENGLAND
关键词
D O I
10.1016/0040-4020(95)00051-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and intramolecular palladium catalysed cycloaddition reactions of diphenylmethylenecyclopropanes 1 and 2 containing olefinic and acetylenic acceptors are described This strategy provides a useful entry into some highly functionalised bicyclo[3.3.0]octane systems.
引用
收藏
页码:3289 / 3302
页数:14
相关论文
共 16 条
[1]   DIARYLMETHYLENE-TETRACYANOETHYLENE CYCLOADDITIONS [J].
BALDWIN, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (10) :1441-&
[2]  
BINGER P, 1987, TOP CURR CHEM, V135, P77
[3]   QUANTITATIVE-EVALUATION OF STERIC EFFECTS IN SN2 RING-CLOSURE REACTIONS [J].
DETAR, DF ;
LUTHRA, NP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (13) :4505-4512
[4]  
ELIEL EL, 1962, STEREOCHEMISTRY CARB, P106
[5]  
HIRAO T, 1984, SYNTHESIS-STUTTGART, P60
[6]   ADDITION OF CYCLOPROPYLPHOSPHONATES TO ALDEHYDES [J].
HIRAO, T ;
NAKAMURA, T ;
HAGIHARA, M ;
AGAWA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5860-5862
[7]  
KIRKBY AJ, 1980, ADV PHYS ORG CHEM, V17, P208
[8]   OBSERVATIONS ON THE INTRAMOLECULAR PALLADIUM(0) CATALYZED [3 + 2] CYCLO-ADDITION OF DIPHENYLMETHYLENECYCLOPROPANES [J].
LEWIS, RT ;
MOTHERWELL, WB ;
SHIPMAN, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (14) :948-950
[9]   AN IMPROVED PREPARATION OF CYCLOPROPYL PHOSPHONATES AND THEIR APPLICATION IN ARYLIDENE CYCLOPROPANE FORMATION [J].
LEWIS, RT ;
MOTHERWELL, WB .
TETRAHEDRON LETTERS, 1988, 29 (39) :5033-5036
[10]   A CONVENIENT SYNTHESIS OF 4,4-DIMETHYLCYCLOPENTENONE [J].
MAGNUS, PD ;
NOBBS, MS .
SYNTHETIC COMMUNICATIONS, 1980, 10 (04) :273-278