Reactions of electron-deficient alkynes and allenes under phosphine catalysis

被引：1026

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

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2001年 / 34卷 / 07期

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

页码：535 / 544

页数：10

共 65 条

[1] Carboxylates as pronucleophiles in the phosphine-catalyzed γ-addition reaction
Alvarez-Ibarra, C
Csáky, AG
de la Oliva, CG
[J]. TETRAHEDRON LETTERS, 1999, 40 (48) : 8465 - 8467
[2] Synthesis of γ,δ-didehydrohomoglutamates by the phosphine-catalyzed γ-addition reaction to acetylenic esters
Alvarez-Ibarra, C
Csáky, AG
de la Oliva, CG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) : 3544 - 3547
[3] A SHORT LARGE-SCALE SYNTHESIS OF (+/-)SARKOMYCIN ESTERS
AMRI, H
RAMBAUD, M
VILLIERAS, J
[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
Evans, PA
Roseman, JD
Garber, LT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) : 4880 - 4881
[6] PHOSPHINE CATALYZED SYNTHESIS OF UNSATURATED CYCLIC CARBONATES FROM CARBON-DIOXIDE AND PROPARGYLIC ALCOHOLS
FOURNIER, J
BRUNEAU, C
DIXNEUF, PH
[J]. 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
GUO, C
LU, XY
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) : 394 - 395
[9] REINVESTIGATION ON THE CATALYTIC ISOMERIZATION OF CARBON-CARBON TRIPLE BONDS
GUO, C
LU, XY
[J]. 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
HANAMOTO, T
BABA, Y
INANAGA, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) : 299 - 300

← 1 2 3 4 5 6 7 →