Free-radical functionalisation of vinylcyclopropanes

被引：16

作者：

Andrey, O

Camuzat-Dedenis, B

Chabaud, L

Julienne, K

Landais, Y

Parra-Rapado, L

Renaud, P

机构：

[1] Univ Bordeaux 1, Lab Chim Organ & Organomet, F-33405 Talence, France

[2] Univ Bern, Dept Chem & Biochem, CH-3000 Bern 9, Switzerland

来源：

TETRAHEDRON | 2003年 / 59卷 / 43期

关键词：

D O I：

10.1016/j.tet.2003.09.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Free-radical mediated cyclopropane ring opening of 2-silylbicyclo[3.1.0]hexane 1 has been carried out leading to the corresponding trisubstituted cyclopentenes 5 and 6 in good yield with complete 1,2-stereocontrot. [3+2]-Annulation has also been performed by trapping the resulting radical with electron-rich and electron-poor olefins, leading to the corresponding polycyclic compounds. Further studies on the functionalisation of dihydropyridines and pyrroles using this methodology is also described. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：8543 / 8550

页数：8

相关论文

共 30 条

[1] Desymmetrisation of cyclopentadienylsilane by asymmetric cyclopropanation [J].

Allais, F ;

Angelaud, R ;

Camuzat-Dedenis, B ;

Julienne, K ;

Landais, Y .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (06) :1069-1073

[2] Five-membered ring analogues of shikimic acid [J].

An, M ;

Toochinda, T ;

Bartlett, PA .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1326-1333

[3] Synthesis of pseudo-sugars based on desymmetrization of dienylsilanes. [J].

Angelaud, R ;

Landais, Y .

TETRAHEDRON LETTERS, 1997, 38 (51) :8841-8844

[4] Stereocontrolled access to carba-C-disaccharides via functionalized dienylsilanes. [J].

Angelaud, R ;

Landais, Y ;

ParraRapado, L .

TETRAHEDRON LETTERS, 1997, 38 (51) :8845-8848

[5] KINETIC DETERMINATION OF THE BOND-DISSOCIATION ENERGY D(ME3SICME2CH2-H) AND THE MAGNITUDE OF THE STABILIZATION ENERGY IN A BETA-SILICON-SUBSTITUTED ALKYL RADICAL [J].

AUNER, N ;

WALSH, R ;

WESTRUP, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (03) :207-208

[6] MODEL STUDIES PROBING THE AMINO-CLAISEN REARRANGEMENT APPROACH TO HYDROISOQUINOLINE SYNTHESIS - DEVELOPMENT OF METHODS FOR STEREOCONTROLLED INTRODUCTION OF RESERPINE-E RING-TYPE FUNCTIONALITY [J].

BAXTER, EW ;

LABAREE, D ;

CHAO, S ;

MARIANO, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2893-2904

[7]

BERTRAND MP, 2001, SULFUR CENTERED RADI, V2, P485

[8] The synthesis of diastereo- and enantiomerically pure β-aminocyclopropanecarboxylic acids [J].

Beumer, R ;

Bubert, C ;

Cabrele, C ;

Vielhauer, O ;

Pietzsch, M ;

Reiser, O .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :8960-8969

[9]

Böhm C, 2000, EUR J ORG CHEM, V2000, P2955

[10]

Byers J., 2001, RADICALS ORGANIC SYN, V1, P72, DOI [10.1002/9783527618293.CH5, DOI 10.1002/9783527618293.CH5]