Facile palladium(O)-catalyzed ring expansion reactions of hydroxy methoxyallenyl cyclic compounds via hydropalladation

被引:30
作者
Nagao, Y
Ueki, A
Asano, K
Tanaka, S
Sano, S
Shiro, M
机构
[1] Univ Tokushima, Fac Pharmaceut Sci, Tokushima 7708505, Japan
[2] Rigaku Corp, Akishima, Tokyo 1968666, Japan
关键词
D O I
10.1021/ol010287k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium(0)-catalyzed one-atom ring expansion of various hydroxy methoxyallenyl compounds has been achieved in excellent yields without the use of aryl halides. Hydroxy methoxyallenylisoindolinones, -indanones, and -phthalans have been readily converted to the corresponding isoquinolones, naphthoquinones, and isochromanones in the presence of P(o-tolyl)(3).
引用
收藏
页码:455 / 457
页数:3
相关论文
共 31 条
[1]  
BARBOSA LCD, 1990, J CHEM SOC PERK T 1, P177
[2]  
Camacho DH, 1999, ANGEW CHEM INT EDIT, V38, P3365, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3365::AID-ANIE3365>3.0.CO
[3]  
2-5
[4]   A PALLADIUM-CATALYZED REARRANGEMENT OF 1-VINYL-1-CYCLOBUTANOLS [J].
CLARK, GR ;
THIENSATHIT, S .
TETRAHEDRON LETTERS, 1985, 26 (21) :2503-2506
[5]  
Crisp GT, 1998, CHEM SOC REV, V27, P427
[6]   PHOTOCYCLOADDITIONS OF 2-(TRIMETHYLSILYLOXY)-1,3-BUTADIENE TO 2-CYCLOALKENONES - ACCESS TO THE BASIC PENTALENOLACTONE SKELETON [J].
DEMUTH, M ;
PANDEY, B ;
WIETFELD, B ;
SAID, H ;
VIADER, J .
HELVETICA CHIMICA ACTA, 1988, 71 (06) :1392-1398
[7]   OXIDATIVE ADDITION OF PHENOLS TO PD(PCY3)2 - SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF TRANS-[PD(PCY3)2(H)(OC6H5)].C6H5OH (1) AND TRANS-[PD(PCY3)2(H)(OC6F5)].C6F5OH (2) [J].
DIBUGNO, C ;
PASQUALI, M ;
LEONI, P ;
SABATINO, P ;
BRAGA, D .
INORGANIC CHEMISTRY, 1989, 28 (07) :1390-1394
[8]  
Hegedus LS, 2000, SYNTHESIS-STUTTGART, P953
[9]  
Hesse M., 1991, RING ENLARGEMENT ORG
[10]   Novel heterocyclic ring-expansion and/or dehydration-hydration reactions of propargylic and allenylic hydroxy γ-lactams in the presence of strong base or Lewis acid [J].
Jeong, IY ;
Lee, WS ;
Goto, S ;
Sano, S ;
Shiro, M ;
Nagao, Y .
TETRAHEDRON, 1998, 54 (48) :14437-14454