Efficient Horner-Wadsworth-Emmons intramolecular cyclisation of a N-substituted phthalimide promoted by KF-Alumina: a general tool for the synthesis of functionalised isoindolinones

被引：34

作者：

Pace, Vittorio ^{[1
]}

Martinez, Fernando ^{[1
]}

Nova, Clara I. ^{[2
]}

Fernandez, Maria ^{[1
]}

Vicente Sinisterra, Jose ^{[1
,2
]}

Alcantara, Andres R. ^{[1
,2
]}

机构：

[1] Univ Complutense, Dept Organ & Pharmaceut Chem, Fac Pharm, E-28040 Madrid, Spain

[2] SBI, Madrid, Spain

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 25期

关键词：

Horner-Wadsworth-Emmons reaction; Isoindolinones; Cyclisation; Heterogeneous catalysis; Enones; ORGANIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE ROUTE; SUPPORTED REAGENTS; DERIVATIVES; ISOINDOLIN-1-ONES; CONDENSATION; WITTIG; PHTHALALDEHYDE; REARRANGEMENT;

D O I：

10.1016/j.tetlet.2009.04.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An intramolecular Horner-Wadsworth-Emmons reaction promoted by KF-Alumina involving a N-substituted phthalimide, cleanly and efficiently furnishes an interesting alpha,beta-unsaturated tricyclic enone which may undergo selective alkylations at the alpha'-position. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3050 / 3053

页数：4

共 53 条

[1] Flash vacuum pyrolysis of stabilised phosphorus ylides .7. Cyclisation of amino acid derived alpha-phthalimidoacyl ylides to give pyrroloisoindolediones [J].

Aitken, RA ;

Cooper, HR ;

Mehrotra, AP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (05) :475-483

[2] Recent advances in KF/alumina promoted organic reactions [J].

Basu, Basudeb ;

Das, Pralay ;

Das, Sajal .

CURRENT ORGANIC CHEMISTRY, 2008, 12 (02) :141-158

[3] SYNTHESIS OF PYRROLIZIDINEDIONES FROM CYCLIC N,N-DIACYLAMINO ACIDS [J].

BESTMANN, HJ ;

MOENIUS, T ;

SOLIMAN, F .

CHEMISTRY LETTERS, 1986, (09) :1527-1528

[4] THE MICHAELIS-ARBUZOV REARRANGEMENT [J].

BHATTACHARYA, AK ;

THYAGARAJAN, G .

CHEMICAL REVIEWS, 1981, 81 (04) :415-430

[5] KF/Al2O3 mediated organic synthesis [J].

Blass, BE .

TETRAHEDRON, 2002, 58 (46) :9301-9320

[6]

BOULLET FM, 1985, TETRAHEDRON, V41, P1259

[7] REDUCTION OF PHTHALIC ACID AND ITS DERIVATIVES BY ZINC [J].

BREWSTER, JH ;

FUSCO, AM ;

CORMAN, BG ;

CAROSINO, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :498-&

[8] 1-Phthalimido-4-(3-indolyl)-2-siloxy-1,3-butadienes:: synthesis and Diels-Alder reactivity [J].

Caballero, E ;

Alonso, D ;

Peláez, R ;

Alvarez, C ;

Puebla, P ;

Sanz, F ;

Medarde, M ;

Tomé, F .

TETRAHEDRON LETTERS, 2004, 45 (08) :1631-1634

[9] MECHANISM OF REACTION BETWEEN TRIALKYL PHOSPHITES AND ALPHA-HALOGENATED KETONES [J].

CHOPARD, PA ;

CLARK, VM ;

HUDSON, RF ;

KIRBY, AJ .

TETRAHEDRON, 1965, 21 (08) :1961-&

[10] LDA-induced metalation of isoindolinones. An efficient route to 3-substituted isoindoline derivatives [J].

Couture, A ;

Deniau, E ;

Ionescu, D ;

Grandclaudon, P .

TETRAHEDRON LETTERS, 1998, 39 (16) :2319-2320

← 1 2 3 4 5 6 →