Palladium-catalyzed [3+2] intramolecular cycloaddition of alk-5-ynylidenecyclopropanes:: A rapid, practical approach to bicyclo[3.3.0]octenes

被引：86

作者：

Delgado, A

Rodríguez, JR

Castedo, L

Mascareñas, JL

机构：

[1] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15782, Spain

[2] Univ Santiago de Compostela, CSIC, Unidad Asociada, Santiago De Compostela 15782, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 31期

关键词：

D O I：

10.1021/ja0356333

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Readily accessible hex-5-ynylidenecyclopropane derivatives cycloisomerize to bicyclic five-membered carbocycles upon heating with catalytic amounts of a palladium complex. Copyright © 2003 American Chemical Society.

引用

页码：9282 / 9283

页数：2

共 17 条

[1]

BAPUJI SA, 1989, TETRAHEDRON LETT, V30, P7107

[2]

BINGER P, 1987, TOP CURR CHEM, V135, P77

[3] 4-METHYLENE-1-CYCLOPENTENES FROM METHYLENECYCLOPROPANES AND ALKYNYLTRIMETHYLSILANES [J].

BINGER, P ;

LU, QH ;

WEDEMANN, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (04) :316-317

[4] INTRAMOLECULAR PALLADIUM-CATALYZED [3+2] CYCLOADDITIONS OF METHYLENECYCLOPROPANES WITH ACETYLENIC ACCEPTORS [J].

CORLAY, H ;

LEWIS, RT ;

MOTHERWELL, WB ;

SHIPMAN, M .

TETRAHEDRON, 1995, 51 (11) :3303-3318

[5] Palladium(0)-catalyzed allylation of 2,2′-dihydroxybiphenyl by 1-ethenyl-cyclopropyl sulfonates:: Preparation of 2,2′-bis(cyclopropylideneethoxy) biphenyls [J].

Delogu, G ;

Salaün, J ;

de Candia, C ;

Fabbri, D ;

Piras, PP ;

Ollivier, J .

SYNTHESIS-STUTTGART, 2002, (15) :2271-2279

[6] STEREOCHEMICAL CONTROL IN METAL-CATALYZED [3+2] CYCLOADDITIONS OF METHYLENECYCLOPROPANES [J].

LAUTENS, M ;

REN, Y ;

DELANGHE, PHM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8821-8822

[7] Transition metal catalyzed stereospecific intramolecular [3+2] cycloadditions of methylenecyclopropanes with alkynes [J].

Lautens, M ;

Ren, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (40) :9597-9605

[8]

LAUTENS M, 1997, HOUBEN WEYL EC, V17, P2217

[9]

Nakamura I, 2002, ADV SYNTH CATAL, V344, P111, DOI 10.1002/1615-4169(200202)344:2<111::AID-ADSC111>3.0.CO

[10]

2-0

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