Cleavage of a carbon-carbon triple bond via gold-catalyzed cascade cyclization/oxidative cleavage reactions of (Z)-enynols with molecular oxygen

被引：172

作者：

Liu, Yuanhong ^{[1
]}

Song, Feijie ^{[1
]}

Guo, Shenghai ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 35期

关键词：

D O I：

10.1021/ja062610q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly efficient carbon-carbon triple bond cleavage reaction of (Z)-enynols was developed, which offered a new route to highly substituted butenolides. The methodology is realized by a tandem reaction using a single gold(I) catalyst, which could catalyze different reactions of cyclization/oxidative cleavage in the same vessel. Copyright © 2006 American Chemical Society.

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页码：11332 / 11333

页数：2

相关论文

共 35 条

[21] Gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols:: Highly efficient synthesis of fully substituted dihydrofurans and furans [J].

Liu, YH ;

Song, FJ ;

Song, ZQ ;

Liu, MN ;

Yan, B .

ORGANIC LETTERS, 2005, 7 (24) :5409-5412

[22]

MIJS WJ, 1986, ORGANIC SYNTHESES OX

[23] ACTIVATION OF MOLECULAR-OXYGEN - RHODIUM-CATALYZED OXIDATION OF OLEFINS [J].

MIMOUN, H ;

MACHIRANT, MMP ;

SEREEDEROCH, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (17) :5437-5444

[24] MILD OXIDATIVE CLEAVAGE OF ALKYNES USING [BIS(TRIFLUOROACETOXY)IODO]PENTAFLUOROBENZENE [J].

MORIARTY, RM ;

PENMASTA, R ;

AWASTHI, AK ;

PRAKASH, I .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6124-6125

[25]

MORRIS MJ, 1999, METAL CLUSTERS CHEM, V1, P221

[26] Reaction of enol ethers with Alkynes catalyzed by transition metals:: 5-exo-dig versus 6-endo-dig cyclizations via cyclopropyl platinum or gold carbene complexes [J].

Nevado, C ;

Cárdenas, DJ ;

Echavarren, AM .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (11) :2627-2635

[27] SURREPTITIOUS INVOLVEMENT OF A METALLACYCLE SUBSTITUENT IN METAL-MEDIATED ALKYNE CLEAVAGE CHEMISTRY [J].

OCONNOR, JM ;

PU, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (24) :9013-9015

[28] Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen [J].

Punniyamurthy, T ;

Velusamy, S ;

Iqbal, J .

CHEMICAL REVIEWS, 2005, 105 (06) :2329-2363

[29] MECHANISM FOR THE OXIDATIVE CLEAVAGE OF ELECTRON-DEFICIENT ACETYLENES WITH ALKALINE HYDROGEN-PEROXIDE [J].

SAWAKI, Y ;

INOUE, H ;

OGATA, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (04) :1133-1138

[30] PARTIAL OXIDATION OF OLEFINS BY MOLECULAR-OXYGEN CATALYZED BY (ALUMINA)RH(O2) .2. [J].

SCHWARTZ, J ;

MCMILLAN, JW ;

FISCHER, HE .

JOURNAL OF MOLECULAR CATALYSIS, 1992, 74 (1-3) :443-450

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