Phosphine-mediated reductive condensation of γ-acyloxy butynoates:: A diversity oriented strategy for the construction of substituted Furans

被引：154

作者：

Jung, CK ^{[1
]}

Wang, JC ^{[1
]}

Krische, MJ ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 13期

关键词：

D O I：

10.1021/ja049377l

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Exposure of γ-acyloxy butynoates to stoichiometric quantities of triphenylphosphine results in reductive condensation to afford substituted furans, by way of allenic ester intermediates. As γ-acyloxy butynoates are readily obtained through condensation of ethyl propiolate with aldehydes followed by acylation, this method represents a powerful and mechanistically novel protocol for the convergent three-component construction of substituted furans. Copyright © 2004 American Chemical Society.

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页码：4118 / 4119

页数：2

相关论文

共 29 条

[1] OXYPHOSPHORANES WITH AN OXAPHOSPHOLENE RING - ANALYSIS OF THE ACTIVATION BARRIERS OF THE ISOMERIZATION PROCESS [J].

BUONO, G ;

LLINAS, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4532-4540

[2] NUCLEAR MAGNETIC RESONANCE EVIDENCE FOR PATHWAYS OF PSEUDOROTATION IN ALKYLOXYPHOSPHORANES [J].

GORENSTEIN, D ;

WESTHEIMER, FH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) :634-+

[3] A NOVEL DEOXYGENATION-ISOMERIZATION REACTION OF 4-HYDROXY-2-YNOIC ESTERS AND GAMMA-HYDROXY-ALPHA,BETA-YNONES [J].

GUO, C ;

LU, XY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (04) :394-395

[4]

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

[5]

2-F

[6] C-C-bond formation by the palladium-catalyzed cycloisomerization/dimerization of terminal allenyl ketones: Selectivity and mechanistic aspects [J].

Hashmi, ASK ;

Ruppert, TL ;

Knofel, T ;

Bats, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7295-7304

[7]

HASHMI ASK, 1995, CHEM-EUR J, V1, P1581

[8] Regioselective syntheses of substituted furans [J].

Hou, XL ;

Cheung, HY ;

Hon, TY ;

Kwan, PL ;

Lo, TH ;

Tong, SY ;

Wong, HNC .

TETRAHEDRON, 1998, 54 (10) :1955-2020

[9] THERMAL REARRANGEMENT OF ALLENYL KETONES [J].

HUNTSMAN, WD ;

YIN, TK .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (21) :3813-3814

[10] FLASH VACUUM THERMOLYSIS OF BETA-KETO-TRIMETHYLSILYL-ENOL-ETHERS - SYNTHESIS OF ALLENIC AND FURANIC DERIVATIVES [J].

JULLIEN, J ;

PECHINE, JM ;

PEREZ, F ;

PIADE, JJ .

TETRAHEDRON, 1982, 38 (10) :1413-1416