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

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

[61] A new and efficient route to 4-carboxymethylcoumarins mediated by vinyltriphenylphosphonium salt [J].

Yavari, I ;

Hekmat-Shoar, R ;

Zonouzi, A .

TETRAHEDRON LETTERS, 1998, 39 (16) :2391-2392

[62] New one-pot synthesis of tetra-alkoxycarbonylallylidenetriphenylphosphoranes [J].

Yavari, I ;

Baharfar, R .

TETRAHEDRON LETTERS, 1998, 39 (09) :1051-1054

[63]

ZHANG CM, 1995, SYNLETT, P645

[64] PHOSPHINE-CATALYZED CYCLOADDITION OF 2,3-BUTADIENOATES OR 2-BUTYNOATES WITH ELECTRON-DEFICIENT OLEFINS - A NOVEL [3+2]-ANNULATION APPROACH TO CYCLOPENTENES [J].

ZHANG, CM ;

LU, XY .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2906-2908

[65] Asymmetric [3+2] cycloaddition of 2,3-butadienoates with electron-deficient olefins catalyzed by novel chiral 2,5-dialkyl-7-phenyl-7-phosphabicyclo[2.2.1]heptanes [J].

Zhu, GX ;

Chen, ZG ;

Jiang, QZ ;

Xiao, DM ;

Cao, P ;

Zhang, XM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (16) :3836-3837

← 1 2 3 4 5 6 7 →