Ruthenium-catalyzed carbonylative cycloaddition of α-keto lactones with alkenes or alkynes:: The participation of an ester-carbonyl group in cycloaddition reactions as the two-atom assembling unit

被引：38

作者：

Chatani, N ^{[1
]}

Amako, K ^{[1
]}

Tobisu, M ^{[1
]}

Asaumi, T ^{[1
]}

Fukumoto, Y ^{[1
]}

Murai, S ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 04期

关键词：

D O I：

10.1021/jo0267495

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of benzofuran-2,3-dione derivatives 1 with CO and alkenes (or alkynes) results in a carbonylative [2+2+1] cycloaddition in which the ester-carbonyl group is incorporated into a two-atom assembling unit to give spirolactone derivatives 2. This reaction provides the first example of an ester-carbonyl group participating in a carbonylative cycloaddition reaction.

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页码：1591 / 1593

页数：3

相关论文

共 28 条

[1]

Bach T, 1997, LIEBIGS ANN-RECL, P1627

[2] Ru3(CO)12-catalyzed cyclocarbonylation of yne-aldehydes to bicyclic α,β-unsaturated γ-butyrolactones [J].

Chatani, N ;

Morimoto, T ;

Fukumoto, Y ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (21) :5335-5336

[3] Ru3(CO)12-catalyzed reaction of yne-imines with carbon monoxide leading to bicyclic α,β-unsaturated lactams [J].

Chatani, N ;

Morimoto, T ;

Kamitani, A ;

Fukumoto, Y ;

Murai, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 579 (1-2) :177-181

[4]

Chatani N, 2000, SYNTHESIS-STUTTGART, P925

[5] Direct synthesis of fused, bicyclic gamma-butyrolactones via tandem reductive cyclization-carbonylation of tethered enals and enones [J].

Crowe, WE ;

Vu, AT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) :1557-1558

[6]

Deslongchamps P., 1983, Stereoelectronic Effects in Organic Chemistry

[7] Metal-assisted cycloaddition reactions in organotransition metal chemistry [J].

Fruhauf, HW .

CHEMICAL REVIEWS, 1997, 97 (03) :523-596

[8] One-pot ruthenium catalyzed synthesis of spiro[pyrrolidin-2-one] derivatives by a [2+2+1] cycloaddition of ketimines, carbon monoxide and ethylene [J].

Göbel, A ;

Imhof, W .

CHEMICAL COMMUNICATIONS, 2001, (07) :593-594

[9] Titanocene-catalyzed cyclocarbonylation of o-allyl aryl ketones to gamma-butyrolactones [J].

Kablaoui, NM ;

Hicks, FA ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) :4424-4431

[10] Diastereoselective synthesis of gamma-butyrolactones from enones mediated or catalyzed by a titanocene complex [J].

Kablaoui, NM ;

Hicks, FA ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) :5818-5819