Synthesis of different ring-size heterocycles from the same propargyl alcohol derivative by ligand effect on Pd(0)

被引:65
作者
Kozawa, Y [1 ]
Mori, M [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
关键词
allenylpalladium complex; eta(3)-propargylpalladium complex; hetercycles; pi-allylpalladium complex; DPPF;
D O I
10.1016/S0040-4039(02)00043-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The type of ligand oil in an allenylpalladium complex, which was prepared from propargyl alcohol derivative and Pd(0), plays an important role in determination of the ring size of the cyclized compound. An intermediary palladium complex bearing a monodentate ligand gave a cyclized compound via palladacycle, while that bearing a bidentate ligand gave one-carbon elongated cyclized compound via a eta(3)-propargylalladium complex. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1499 / 1502
页数:4
相关论文
共 14 条
[1]   eta(3)-Propargyl/allenyl complexes of platinum and palladium of the type [(PPh(3))(2)M(eta(3)-CH(2)CCR)](+) [J].
Baize, MW ;
Blosser, PW ;
Plantevin, V ;
Schimpff, DG ;
Gallucci, JC ;
Wojcicki, A .
ORGANOMETALLICS, 1996, 15 (01) :164-173
[2]   Kinetic addition of nucleophiles to η3-propargyl rhenium complexes occurs at the central carbon to produce rhenacyclobutenes [J].
Casey, CP ;
Nash, JR ;
Yu, CS ;
Selmeczy, AD ;
Chung, S ;
Powell, DR ;
Hayashi, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :722-733
[3]  
FournierNguefack C, 1996, SYNLETT, P553
[4]   Efficient synthesis of 4-ethenylidene-2-oxazolidinones via palladium-catalyzed aminocyclization of 2-butyn-1,4-diol biscarbamates [J].
Kimura, M ;
Wakamiya, Y ;
Horino, Y ;
Tamaru, Y .
TETRAHEDRON LETTERS, 1997, 38 (22) :3963-3966
[5]  
KZOAWA Y, 2001, TETRAHEDRON LETT, V42, P4869
[6]   An easy palladium-catalyzed access to 2-alkylidene-1,4-benzodioxanes [J].
Labrosse, JR ;
Lhoste, P ;
Sinou, D .
TETRAHEDRON LETTERS, 1999, 40 (51) :9025-9028
[7]   A simple and efficient enantioselective synthesis of 2-alkylidene-3-alkyl-1,4-benzodioxanes by palladium-catalyzed annulation of benzene-1,2-diol and propargylic carbonates [J].
Labrosse, JR ;
Lhoste, P ;
Sinou, D .
ORGANIC LETTERS, 2000, 2 (04) :527-529
[8]   A NEW FURAN ANNELATION REACTION BY THE PALLADIUM-CATALYZED REACTION OF 2-ALKYNYL CARBONATES OR 2-(1-ALKYNYL)OXIRANES WITH BETA-KETO-ESTERS [J].
MINAMI, I ;
YUHARA, M ;
WATANABE, H ;
TSUJI, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 334 (1-2) :225-242
[9]  
Tsuji J, 1995, ANGEW CHEM INT EDIT, V34, P2589
[10]  
Tsuji J., 1995, Palladium Reagents and Catalysts Innovations in Organic Synthesis