A NEW ROUTE TO ALPHA,BETA-UNSATURATED ALDEHYDES USING THE CONDENSATION OF TRIMETHYLSILYL BETA-TRIMETHYLSILYL ENOL ETHERS WITH ALDEHYDES

被引：8

作者：

DUHAMEL, L ^{[1
]}

GRALAK, J ^{[1
]}

BOUYANZER, A ^{[1
]}

机构：

[1] INST RECH CHIM ORGAN FINE,F-76821 MONT ST AIGNAN,FRANCE

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(00)61554-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Beta-trimethylsilyl enol ethers 1 (Z) obtained from beta-bromoenolethers 2 were condensed with aliphatic and aromatic aldehydes in the presence of a catalytic quantity of trimethylsilyl triflate leading to ethylenic aldehydes 3 (E) with good yields (79-90%).

引用

页码：7745 / 7748

页数：4

共 17 条

[1] STEREOSELECTIVE SYNTHESIS OF (E)-ALPHA BETA-UNSATURATED ACIDS FROM C,O,O-TRI(TRIMETHYLSILYL) KETENE ACETAL AND ALDEHYDES [J].

BELLASSOUED, M ;

GAUDEMAR, M .

TETRAHEDRON LETTERS, 1988, 29 (36) :4551-4554

[2] A SIMPLE AND HIGHLY STEREOSELECTIVE ROUTE TO E-ALPHA,BETA-UNSATURATED ALDEHYDES [J].

BELLASSOUED, M ;

MAJIDI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2517-2522

[3]

BOUYANZER A, 1993, THESIS U ROUEN

[4]

COREY EJ, 1976, TETRAHEDRON LETT, P7

[5] ALPHA-SILYL ALDEHYDES - PREPARATION AND NEW PROPERTIES [J].

DUHAMEL, L ;

GRALAK, J ;

NGONO, B .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 363 (1-2) :C4-C6

[6] BETA-LITHIUM CONTAINING ENOL ETHERS - SYNTHESIS OF ALPHA-ETHYLENIC ALDEHYDES [J].

DUHAMEL, L ;

TOMBRET, F ;

MOLLIER, Y .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 280 (01) :1-16

[7] POLYUNSATURATED ALDEHYDES BY DIRECT POLYVINYLOGATION OF CARBONYL-COMPOUNDS USING FUNCTIONALIZED PHOSPHONATES [J].

DUHAMEL, L ;

GUILLEMONT, J ;

LEGALLIC, Y ;

PLE, G ;

POIRIER, JM ;

RAMONDENC, Y ;

CHABARDES, P .

TETRAHEDRON LETTERS, 1990, 31 (22) :3129-3132

[8] PREPARATION OF "BETA-BROMOTRIMETHYLSILOXYENOLETHERS FROM ALPHA-BROMOCARBONYL COMPOUNDS [J].

DUHAMEL, L ;

TOMBRET, F ;

POIRIER, JM .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1985, 17 (02) :99-105

[9]

HUDRLIK PF, 1976, TETRAHEDRON LETT, P1449

[10] ALPHA-KETO DIANIONS - NEW REACTIVE INTERMEDIATES [J].

KOWALSKI, CJ ;

ODOWD, ML ;

BURKE, MC ;

FIELDS, KW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (16) :5411-5412

← 1 2 →