Phosphine-cataiyzed [3+2] cycloaddition reactions of substituted 2-alkynoates or 2,3-allenoates with electron-deficient olefins and imines

被引：127

作者：

Xu, ZR ^{[1
]}

Lu, XY ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 03期

基金：

中国国家自然科学基金;

关键词：

tributylphosphine; 3+2] cycloaddition; cyclopentenes; pyrrolines;

D O I：

10.1016/S0040-4039(98)02405-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of a catalytic amount of tributylphosphine, substituted 2-alkynoates or 2,3-allenoates reacted with electron-deficient olefins and imines at room temperature to afford the [3+2] cycloaddition products in moderate to good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：549 / 552

页数：4

共 16 条

[1] Stereocontrolled synthesis of highly substituted proline esters via [3+2] cycloaddition between N-metalated azomethine ylides and nitroalkenes.: Origins of the metal effect on the stereochemical outcome [J].

Ayerbe, M ;

Arrieta, A ;

Cossío, FP ;

Linden, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1795-1805

[2]

Bird C W., 1984, COMPREHENSIVE HETERO, P89

[3]

Giovannini R, 1998, SYNLETT, P90

[4]

Hayashi M, 1998, ANGEW CHEM INT EDIT, V37, P837, DOI 10.1002/(SICI)1521-3773(19980403)37:6<837::AID-ANIE837>3.0.CO

[5]

2-R

[6] ANIONIC APPROACHES TO THE CONSTRUCTION OF CYCLOPENTANOIDS [J].

HUDLICKY, T ;

PRICE, JD .

CHEMICAL REVIEWS, 1989, 89 (07) :1467-1486

[7] Diastereoselective and enantioselective intramolecular amino-zinc-enolate carbometalation reactions. A new polysubstituted pyrrolidines synthesis [J].

Lorthiois, E ;

Marek, I ;

Normant, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2442-2450

[8] Highly regio- and stereoselective [3+2] cyclopentanone annulation using a 3-(alkylthio)-2-siloxyallyl cationic species [J].

Masuya, K ;

Domon, K ;

Tanino, K ;

Kuwajima, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1724-1731

[9] Synthesis of novel conformationally restricted L-glutamate analogues [J].

Pyne, SG ;

Schafer, K ;

Skelton, BW ;

White, AH .

CHEMICAL COMMUNICATIONS, 1997, (23) :2267-2268

[10] NEUTRAL ALKYLATIONS VIA PALLADIUM(0) CATALYSIS [J].

TROST, BM ;

MOLANDER, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (19) :5969-5972

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