(E)-2-OXO-1-SULFONYL-3-ALKENES AS REACTIVE HETERO 1,3-DIENES - ABSOLUTELY ENDO-SELECTIVE HETERO-DIELS-ALDER REACTIONS WITH VINYL ETHERS IN THE PRESENCE OF A LEWIS-ACID CATALYST

被引：24

作者：

WADA, E ^{[1
]}

YASUOKA, H ^{[1
]}

KANEMASA, S ^{[1
]}

机构：

[1] KYUSHU UNIV, INTERDISCIPLINARY GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN

来源：

CHEMISTRY LETTERS | 1994年 / 01期

关键词：

D O I：

10.1246/cl.1994.145

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(E)-2-Oxo-1-sulfonyl-3-alkenes as new hetero 1,3-dienes undergo smooth hetero Diels-Alder reactions with vinyl ethers in the presence of Eu(fod)3 or TiCl2(i-PrO)2. The reactions are absolutely endo-selective producing 2,4-cis-3,4-dihydro-2H-pyrans in excellent yields, sufficient catalytic cycles being attained. The sulfonyl-stabilized carbanions derived from the cycloadducts are alkylated followed by reductive desulfonylation.

引用

收藏

页码：145 / 148

页数：4

相关论文

共 26 条

[1]

BAKKER CG, 1981, RECL TRAV CHIM PAY B, V100, P13

[2] OXIDATIVE COUPLING .5. CARBON-CARBON BOND FORMATION FROM BETA-KETOSULFONE DIANIONS [J].

BELLETIRE, JL ;

SPLETZER, EG .

SYNTHETIC COMMUNICATIONS, 1987, 17 (14) :1701-1707

[3]

Boger D. L., 1987, ORGANIC CHEM SERIES, V47, P167

[4] 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

[5] 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

[6] A NOVEL REGIOSELECTIVE SYNTHESIS OF ALLYLSILANES [J].

CHAN, TH ;

LABRECQUE, D .

TETRAHEDRON LETTERS, 1991, 32 (09) :1149-1152

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

DANISHEFSKY, S ;

BEDNARSKI, M .

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

[8] 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

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

DESIMONI, G ;

TACCONI, G .

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

[10] CHEMISTRY OF 2-ALKOXY-3,4-DIHYDRO-2H-PYRANS .6. RELATIVE REACTIVITY OF SUBSTITUTED 2-ALKOXY-3,4-DIHYDRO-2H-PYRANS AND 2-PHENOXY-3,4-DIHYDRO-2H-PYRANS WITH TERT-BUTYL HYPOCHLORITE - EFFECT OF SUBSTITUENTS ON REACTIVITY AND PRODUCTS [J].

HALL, SS ;

WEBER, GF ;

DUGGAN, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (04) :667-672