A convenient synthesis of α-methylene-γ-butyrolactones from allenyl carbonyl units mediated by Mo(CO)6 through intramolecular cyclocarbonylation

被引：47

作者：

Yu, CM ^{[1
]}

Hong, YT

Lee, JH

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

[2] Sungkyunkwan Univ, Lab Met Catalyzed React, Suwon 440746, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 24期

关键词：

D O I：

10.1021/jo049252z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel procedure for the synthesis of cis-fused bicyclic alpha-methylene-gamma-butyrolactones from allenyl carbonyl functionalities via the molybdenum-mediated cyclocarbonylation is described. The use Of MO(CO)(6) with DMSO to promote reaction results in an efficient and convenient protocol through the three-component assembly in high yields.

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页码：8506 / 8509

页数：4

相关论文

共 31 条

[1] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[2]

Beller M., 1998, TRANSITION METALS OR, pI

[3] Chiral nonracemic α-alkylidene and α-silylidene cyclopentenones from chiral allenes using an intramolecular allenic Pauson-Khand-type cycloaddition [J].

Brummond, KM ;

Kerekes, AD ;

Wan, HH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5156-5163

[4] A rapid synthesis of hydroxymethylacylfulvene (HMAF) using the allenic Pauson-Khand reaction. A synthetic approach to either enantiomer of this illudane structure [J].

Brummond, KM ;

Lu, JL ;

Petersen, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :4915-4920

[5] 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

[6] PROMOTERS FOR THE (ALKYNE)HEXACARBONYLDICOBALT-BASED CYCLOPENTENONE SYNTHESIS [J].

CHUNG, YK ;

LEE, BY ;

JEONG, N ;

HUDECEK, M ;

PAUSON, PL .

ORGANOMETALLICS, 1993, 12 (01) :220-223

[7] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+

[8] TITANIUM-CATALYZED REDUCTIVE CYCLIZATION OF DELTA,EPSILON-UNSATURATED KETONES AND ALDEHYDES [J].

CROWE, WE ;

RACHITA, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (25) :6787-6788

[9] 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

[10] 25 YEARS OF DIMETHYLSULFOXONIUM METHYLIDE (COREYS REAGENT) [J].

GOLOLOBOV, YG ;

NESMEYANOV, AN ;

LYSENKO, VP ;

BOLDESKUL, IE .

TETRAHEDRON, 1987, 43 (12) :2609-2651

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