Gold(III)- and platinum(II)-catalyzed domino reaction consisting of heterocyclization and 1,2-migration:: Efficient synthesis of highly substituted 3(2H)-furanones

被引：149

作者：

Kirsch, Stefan F. ^{[1
]}

Binder, Joerg T. ^{[1
]}

Liebert, Clemence ^{[1
]}

Menz, Helge ^{[1
]}

机构：

[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 35期

关键词：

cyclization; domino reactions; heterocycles; platinum; rearrangement;

D O I：

10.1002/anie.200601836

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) PtCl2-catalyzed alkyne activation initiates a domino reaction, in which a heterocyclization is followed by a 1,2-alkyl migration, for the construction of a variety of substituted 3(2H)-furanones. This stereospecific reaction is proposed to proceed through an oxonium ion intermediate (see scheme). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5878 / 5880

页数：3

共 43 条

[11] Pt(II) or Ag(I) salt catalyzed cycloisomerizations and tandem cycloadditions forming functionalized azacyclic arrays [J].

Harrison, TJ ;

Dake, GR .

ORGANIC LETTERS, 2004, 6 (26) :5023-5026

[12]

Hashmi A. S. K., 2005, ANGEW CHEM, V117, P2858

[13]

Hashmi A.S.K., 2000, ANGEW CHEM, V112, P2382, DOI DOI 10.1002/CCTC.200900237

[14]

Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P2285, DOI 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO

[15]

2-F

[16] Gold catalysis:: Proof of arene oxides as intermediates in the phenol synthesis [J].

Hashmi, ASK ;

Rudolph, M ;

Weyrauch, JP ;

Wöelfle, M ;

Frey, W ;

Bats, JW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) :2798-2801

[17]

Hashmi ASK, 2004, GOLD BULL, V37, P51

[18] Homogeneous gold catalysts and alkynes: A successful liaison [J].

Hashmi, ASK .

GOLD BULLETIN, 2003, 36 (01) :3-9

[19] The catalysis gold rush: New claims [J].

Hashmi, ASK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (43) :6990-6993

[20] The golden gate to catalysis [J].

Hoffmann-Röder, A ;

Krause, N .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (03) :387-391

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