Reactions of electron-deficient alkynes and allenes under phosphine catalysis

被引:1027
作者
Lu, XY [1 ]
Zhang, CM [1 ]
Xu, ZR [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ar000253x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The development of some new synthetic reactions derived from nucleophilic addition of phosphines to electron-deficient carbon-carbon triple bonds is described. These reactions show that the phosphine plays the role of a nucleophile as well as an excellent leaving group. The central problem is to generate a 1,3-dipole from atkynoates or allenoates; (2,3-butadienoates) by interaction with various phosphines. This study illuminates the unusual phenomena and shows how this understanding allows control of the reaction.
引用
收藏
页码:535 / 544
页数:10
相关论文
共 65 条
[1]   Carboxylates as pronucleophiles in the phosphine-catalyzed γ-addition reaction [J].
Alvarez-Ibarra, C ;
Csáky, AG ;
de la Oliva, CG .
TETRAHEDRON LETTERS, 1999, 40 (48) :8465-8467
[2]   Synthesis of γ,δ-didehydrohomoglutamates by the phosphine-catalyzed γ-addition reaction to acetylenic esters [J].
Alvarez-Ibarra, C ;
Csáky, AG ;
de la Oliva, CG .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3544-3547
[3]   A SHORT LARGE-SCALE SYNTHESIS OF (+/-)SARKOMYCIN ESTERS [J].
AMRI, H ;
RAMBAUD, M ;
VILLIERAS, J .
TETRAHEDRON LETTERS, 1989, 30 (52) :7381-7382
[4]  
CRISTAU HJ, 1985, B SOC CHIM FR, P980
[5]   An iterative approach to biologically important fused polycyclic ethers via acyl radical cyclizations [J].
Evans, PA ;
Roseman, JD ;
Garber, LT .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :4880-4881
[6]   PHOSPHINE CATALYZED SYNTHESIS OF UNSATURATED CYCLIC CARBONATES FROM CARBON-DIOXIDE AND PROPARGYLIC ALCOHOLS [J].
FOURNIER, J ;
BRUNEAU, C ;
DIXNEUF, PH .
TETRAHEDRON LETTERS, 1989, 30 (30) :3981-3982
[7]  
GENDRE PL, 1996, J ORG CHEM, V61, P8453
[8]   A NOVEL DEOXYGENATION-ISOMERIZATION REACTION OF 4-HYDROXY-2-YNOIC ESTERS AND GAMMA-HYDROXY-ALPHA,BETA-YNONES [J].
GUO, C ;
LU, XY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) :394-395
[9]   REINVESTIGATION ON THE CATALYTIC ISOMERIZATION OF CARBON-CARBON TRIPLE BONDS [J].
GUO, C ;
LU, XY .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (16) :1921-1923
[10]   UTILITY OF PHOSPHONIUM-SUBSTITUTED ESTER ENOLATES AS SYNTHETIC INTERMEDIATES - A NOVEL TRIALKYLPHOSPHINE-CATALYZED [3,3] REARRANGEMENT OF ALLYLIC ACRYLATES [J].
HANAMOTO, T ;
BABA, Y ;
INANAGA, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :299-300