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

[11] An enantioselective Baylis-Hillman reaction catalyzed by chiral phosphines under atmospheric pressure [J].

Hayase, T ;

Shibata, T ;

Soai, K ;

Wakatsuki, Y .

CHEMICAL COMMUNICATIONS, 1998, (12) :1271-1272

[12]

Hudson H. R, 1990, CHEM ORGANOPHOSPHORU, V1, P385

[13]

IMAYAWA T, 1984, SYNTHETIC COMMUN, V14, P1267

[14] ORGANIC-SYNTHESIS WITH TRIALKYLPHOSPHINE CATALYSTS - CONJUGATE ADDITION OF ALCOHOLS TO ALPHA,BETA-UNSATURATED ALKYNIC ACID-ESTERS [J].

INANAGA, J ;

BABA, Y ;

HANAMOTO, T .

CHEMISTRY LETTERS, 1993, (02) :241-244

[15] CATALYTIC FORMATION OF CONJUGATED DIENONES FROM YNONES BY A RUTHENIUM COMPLEX [J].

INOUE, Y ;

IMAIZUMI, S .

JOURNAL OF MOLECULAR CATALYSIS, 1988, 49 (01) :L19-L21

[16]

JOURNIER JM, 1991, J CHEM SOC P1, P3271

[17] A short synthesis of conjugated unsaturated amides and esters via triphenylphosphine-catalysed isomerisation of acetylenic pentafluorophenyl esters [J].

Kazmaier, U .

CHEMICAL COMMUNICATIONS, 1997, (23) :2305-2306

[18] A short synthesis of conjugated unsaturated alcohols [J].

Kazmaier, U .

TETRAHEDRON, 1998, 54 (08) :1491-1496

[19]

Kirby A. J., 1967, ORGANIC CHEM PHOSPHO

[20]

KITAZUME S, 1977, Patent No. 77105115

← 1 2 3 4 5 6 7 →