Intramolecular Michael reactions by iron(III) catalysis

被引：35

作者：

Christoffers, J ^{[1
]}

Oertling, H ^{[1
]}

机构：

[1] Tech Univ Berlin, Inst Organ Chem, D-10623 Berlin, Germany

来源：

TETRAHEDRON | 2000年 / 56卷 / 10期

关键词：

annulation; catalysis; iron compounds; Michael reactions;

D O I：

10.1016/S0040-4020(00)00045-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Seven-membered ring annulation is achieved by an intramolecular Michael reaction catalyzed by iron(III) chloride hexahydrate. Reaction conditions are mild and non-basic, and chemo- and stereoselectivity is excellent. Contrastingly, this method fails for a 17-membered ring annulation. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1339 / 1344

页数：6

共 32 条

[1] Bergmann E.D., 1959, ORG REACTIONS, V10, P179
[2] BERTHIAUME G, 1995, B SOC CHIM FR, V132, P371
[3] INTRAMOLECULAR MICHAEL ADDITION OF CYCLIC BETA-KETOESTER ON CONJUGATED OLEFINIC KETONE, A STEREOELECTRONICALLY CONTROLLED PROCESS
BERTHIAUME, G
LAVALLEE, JF
DESLONGCHAMPS, P
[J]. TETRAHEDRON LETTERS, 1986, 27 (45) : 5451 - 5454
[4] COPE REARRANGEMENT - REACTION FOR REPEATABLE RING EXPANSIONS
BRUHN, J
HEIMGARTNER, H
SCHMID, H
[J]. HELVETICA CHIMICA ACTA, 1979, 62 (08) : 2630 - 2654
[5] Cainelli G., 1984, CHROMIUM OXIDATIONS
[6] Iron(III) catalysis of an intramolecular Michael reaction
Christoffers, J
[J]. TETRAHEDRON LETTERS, 1998, 39 (39) : 7083 - 7084
[7] Christoffers J, 1998, EUR J ORG CHEM, V1998, P759, DOI 10.1002/(SICI)1099-0690(199805)1998:5<759::AID-EJOC759>3.0.CO
[8] 2-W
[9] An enone-dienol tautomerism and an iron(III)-catalyzed dimerization of cycloalkenone-2-carboxylates
Christoffers, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) : 4539 - 4540
[10] Christoffers J, 1998, EUR J ORG CHEM, V1998, P1259

← 1 2 3 4 →