LEWIS ACID-CATALYZED HETERO-DIELS-ALDER REACTIONS OF METHYL 2-OXO-3-ALKENOATES WITH ALKENES

被引：17

作者：

SERA, A

OHARA, M

YAMADA, H

EGASHIRA, E

UEDA, N

SETSUNE, J

机构：

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1994年 / 67卷 / 07期

关键词：

D O I：

10.1246/bcsj.67.1912

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lewis acid-catalyzed cycloadditions of 4-substituted methyl 2-oxo-3-butenoates and -3-pentenoates with alkenes took place with high regio- and stereoselectivities to afford substituted 6-methoxycarbonyl-3,4-dihydro-2H-pyrans in good to moderate yields. None of the ene products were produced. Similar reactions of methyl 3-phenyl-2-oxo-3-butenoate with alkenes afforded both the corresponding 3,4-dihydro-2H-pyrans and a dimeric cycloadduct of the diene component. The regio- and stereoselectivities of the present inverse-electron-demand cycloadditions indicated that the reactions proceeded through a concerted exo transition state.

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页码：1912 / 1917

页数：6

相关论文

共 32 条

[1] A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF DL-OLEANDROSE [J].

BERTI, G ;

CATELANI, G ;

COLONNA, F ;

MONTI, L .

TETRAHEDRON, 1982, 38 (20) :3067-3072

[2] ACCELERATED INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 1-OXA-1,3-BUTADIENES - [4 + 2] CYCLO-ADDITION REACTIONS OF BETA-GAMMA-UNSATURATED ALPHA-KETO ESTERS [J].

BOGER, DL ;

ROBARGE, KD .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3373-3377

[3] A DIVERGENT DENOVO SYNTHESIS OF CARBOHYDRATES BASED ON AN ACCELERATED INVERSE ELECTRON DEMAND DIELS-ALDER REACTION OF 1-OXA-1,3-BUTADIENES [J].

BOGER, DL ;

ROBARGE, KD .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5793-5796

[4]

BRUGIDOU J, 1963, CR HEBD ACAD SCI, V256, P3323

[5] LANTHANIDE CATALYSIS OF CYCLO-ADDITIONS OF HETERODIENES WITH ENOL ETHERS [J].

DANISHEFSKY, S ;

BEDNARSKI, M .

TETRAHEDRON LETTERS, 1984, 25 (07) :721-724

[6] ORGANIC-REACTIONS AT HIGH-PRESSURE - CYCLOADDITIONS WITH ENOL AND DIENOL DERIVATIVES [J].

DAUBEN, WG ;

KRABBENHOFT, HO .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (02) :282-287

[7] A NEW SYNTHESIS OF FUNCTIONALIZED 6,8-DIOXABICYCLO[3.2.1]OCTANES [J].

DAUDE, N ;

EGGERT, U ;

HOFFMANN, HMR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (03) :206-207

[8] HETERODIENE SYNTHESES WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

DESIMONI, G ;

TACCONI, G .

CHEMICAL REVIEWS, 1975, 75 (06) :651-692

[9] CYCLOADDITION REACTIONS OF ARYLMETHYLENEMALONALDEHYDES - AN APPROACH TO 4-ARYL-3,4-DIHYDRO-2H-PYRAN-5-CARBOXALDEHYDES [J].

DVORAK, D ;

ARNOLD, Z .

TETRAHEDRON LETTERS, 1982, 23 (42) :4401-4402

[10] PHEROMONE SYNTHESES - MODEL REACTIONS FOR THE SYNTHESIS OF POLYETHER ANTIBIOTICS [J].

IRELAND, RE ;

HABICH, D .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (04) :1418-1427

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