Palladium-catalyzed cyclization reaction of allylic bromides with 1,2-dienyl ketones. An efficient synthesis of 3-allylic polysubstituted furans

被引：130

作者：

Ma, SM ^{[1
]}

Li, LT ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 07期

关键词：

D O I：

10.1021/ol0055871

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 3-Allylic polysubstituted furans were synthesized via a palladium-catalyzed cyclization reaction of allylic bromides with differently substituted 1,2-allenyl ketones. This process may occur via the reaction of a furanyl palladium intermediate with allylic bromide.

引用

页码：941 / 944

页数：4

共 56 条

[1] Synthesis of functionalised furans and pyrroles through annulation reactions of 4-pentynones. [J].

Arcadi, A ;

Rossi, E .

TETRAHEDRON, 1998, 54 (50) :15253-15272

[2]

Benassi R. Furans, 1996, COMPREHENSIVE HETERO, V2, P259

[3] An efficient synthesis of 2,3,5-trisubstituted furans from α,β-unsaturated ketones [J].

Brown, CD ;

Chong, JM ;

Shen, LX .

TETRAHEDRON, 1999, 55 (50) :14233-14242

[4]

BUCHI G, 1969, J ORG CHEM, V34, P857

[5] Synthesis of 2,5-disubstituted furans via palladium-catalyzed annulation of alkyl 3-oxo-6-heptynoates [J].

Cacchi, S ;

Fabrizi, G ;

Moro, L .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5327-5332

[6] A NEW SYNTHESIS OF SUBSTITUTED FURANS [J].

DANHEISER, RL ;

STONER, EJ ;

KOYAMA, H ;

YAMASHITA, DS ;

KLADE, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4407-4413

[7]

Dean F. M., 1984, COMPREHENSIVE HETERO, V4, P531, DOI DOI 10.1016/B978-008096519-2.00060-6

[8]

DHAVALIKAR RS, 1966, INDIAN J BIOCHEM, V3, P144

[9]

Donnelly D.M. X., 1984, COMPREHENSIVE HETERO, V4, P657, DOI DOI 10.1016/B978-008096519-2.00062-X

[10] Magnesium mediated carbometallation of propargyl alcohols: direct routes to furans and furanones [J].

Forgione, P ;

Wilson, PD ;

Fallis, AG .

TETRAHEDRON LETTERS, 2000, 41 (01) :17-20

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