Indium-trichloride catalyzed Michael reaction of silyl enol ethers with α,β-unsaturated carbonyl compounds under neat condition

被引：57

作者：

Loh, TP ^{[1
]}

Wei, LL ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 119260, Singapore

来源：

TETRAHEDRON | 1998年 / 54卷 / 26期

关键词：

Michael reaction; indium trichloride; neat condition;

D O I：

10.1016/S0040-4020(98)00394-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of a catalytic amount of indium (III) trichloride (InCl3) (20 mol%), ketene silyl enol ethers react quickly with alpha, beta-unsaturated ketones and esters to afford the corresponding Michael adducts in moderate to good yields. Indium(III) trichloride can be recovered and reused without decrease in yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7615 / 7624

页数：10

共 24 条

[1]

Bergmann E.D., 1959, ORG REACTIONS, V10, P179

[2]

DITTMER DC, 1998, CHEM IND, P779

[3] LEWIS ACID-CATALYZED MICHAEL-TYPE ADDITION - A NEW REGIOSELECTIVE AND DIASTEREOSELECTIVE ANNULATION METHOD USING METHYL VINYL KETONE [J].

DUHAMEL, P ;

DUJARDIN, G ;

HENNEQUIN, L ;

POIRIER, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (03) :387-396

[4] SPECIFIC ENOLATES FROM ALPHA-AMINO KETONES [J].

GARST, ME ;

BONFIGLIO, JN ;

GRUDOSKI, DA ;

MARKS, J .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (12) :2307-2315

[5] CONDENSATION OF KETENE ACETALS DERIVED FROM GLYCOLATES WITH ALDEHYDES AND KETONES - SYNTHESIS OF ALPHA,BETA-DIALKOXY ESTERS [J].

GRAY, BD ;

WHITE, JD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (01) :20-21

[6] ACYCLIC STEREOSELECTION .29. STEREOSELECTION IN THE MICHAEL ADDITION-REACTION .1. THE MOKAIYAMA MICHAEL RECTION [J].

HEATHCOCK, CH ;

NORMAN, MH ;

UEHLING, DE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (09) :2797-2799

[7] A SILYL ENOL ETHER VARIATION OF THE ROBINSON ANNULATION [J].

HUFFMAN, JW ;

POTNIS, SM ;

SATISH, AV .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4266-4270

[8] AN ESSENTIALLY MILD AND EFFICIENT CATALYST SYSTEM FOR THE ACTIVATION OF CARBONYL-COMPOUNDS AND THEIR DERIVATIVES - THE COMBINED USE OF TRIMETHYLSILYL CHLORIDE AND TIN(II) CHLORIDE [J].

IWASAWA, N ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1987, (03) :463-466

[9] NOVEL REACTIVE SILYL ENOLATES - HIGHLY STEREOSELECTIVE ALDOL AND MICHAEL REACTIONS WITHOUT CATALYSTS [J].

KOBAYASHI, S ;

NISHIO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2647-2649

[10]

KOBAYASHI S, 1993, SYNLETT, P472

← 1 2 3 →