REACTIVITY OF 2-METHYLENE-1,3-DICARBONYL COMPOUNDS - INVERSE ELECTRON-DEMAND DIELS-ALDER REACTIONS WITH ALKYL VINYL ETHERS

被引：20

作者：

YAMAUCHI, M

KATAYAMA, S

BABA, O

WATANABE, T

机构：

[1] Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 11期

关键词：

D O I：

10.1039/p19900003041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly regioselective hetero-Diels-Alder reactions were achieved by reaction of 2-methylene-1,3dicarbonyl compounds 1 with alkyl vinyl ethers 2. This regioselectivity of the cycloadditions was consistent with the results that could be predicted by considering the frontier orbital of 1.

引用

收藏

页码：3041 / 3044

页数：4

相关论文

共 18 条

[1] ORGANIC LEWIS-ACIDS .34. THERMAL [4-PI + 2-PI]-CYCLOADDITION OF ENOL ETHERS TO 1,1-DICARBONYL SUBSTITUTED ETHENES [J].

BITTER, J ;

LEITICH, J ;

PARTALE, H ;

POLANSKY, OE ;

RIEMER, W ;

RITTERTHOMAS, U ;

SCHLAMANN, B ;

STILKERIEG, B .

CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (03) :1020-1032

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

DESIMONI, G ;

TACCONI, G .

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

[3] 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

[4]

FLEMING I, 1976, FRONTIER ORBITALS OR, P114

[5]

Gagnaire D., 1963, B SOC CHIM FR, P2633

[6] 6-ALKOXY-3,4-DIHYDRO-2H-PYRANS FROM SUBSTITUTED ALPHA,BETA-UNSATURATED ESTERS [J].

HALL, HK ;

RASOUL, HAA ;

GILLARD, M ;

ABDELKADER, M ;

NOGUES, P ;

SENTMAN, RC .

TETRAHEDRON LETTERS, 1982, 23 (06) :603-606

[7] A CORRELATION OF REACTION RATES [J].

HAMMOND, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (02) :334-338

[8] FRONTIER MOLECULAR-ORBITAL THEORY OF CYCLOADDITION REACTIONS [J].

HOUK, KN .

ACCOUNTS OF CHEMICAL RESEARCH, 1975, 8 (11) :361-369

[9] PREPARATION AND DIELS-ALDER REACTIONS OF 1,1-DICARBONYLALKENES [J].

HOYE, TR ;

CARUSO, AJ ;

MAGEE, AS .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (21) :4152-4156

[10] THEORETICAL-STUDIES OF CONFORMATIONS OF ACROLEIN, ACRYLIC-ACID, METHYL ACRYLATE, AND THEIR LEWIS ACID COMPLEXES [J].

LONCHARICH, RJ ;

SCHWARTZ, TR ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) :14-23