The ruthenium catalyzed formation of chiral dihydropyrrolones from α,β-unsaturated imines:: extending the reaction to terminal alkenes and investigating the formation of pyrroles as side-products

被引：28

作者：

Dönnecke, D ^{[1
]}

Imhof, W ^{[1
]}

机构：

[1] Univ Jena, Inst Inorgan & Analyt Chem, D-07743 Jena, Germany

来源：

TETRAHEDRON | 2003年 / 59卷 / 43期

关键词：

catalysis; C-H activation; ruthenium; pyrrolones; pyrroles;

D O I：

10.1016/j.tet.2003.09.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of alpha,beta-unsaturated imines derived from cinnamaldehyde with CO and various alkenes produces chiral 1,3-dihydropyrrolone derivatives. As a byproduct the formation of 2,3-disubstituted pyrroles is observed in every reaction. If the imines are reacted with ethylene only, products with an ethyl group at C-3 of the imine chain are formed. The implications of these findings on the reaction mechanism are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8499 / 8507

页数：9

共 39 条

[11] ANTIINFLAMMATORY 2,3-DIHYDRO-1H-PYRROLIZINES .9. SYNTHESIS AND OXIDATION OF (2,3-DIHYDRO-6,7-DIPHENYL-1H-PYRROLIZIN-5-YL)ACETALDEHYDE (DADHP-5-ACETALDEHYDE) [J].

DANNHARDT, G ;

STEINDL, L .

ARCHIV DER PHARMAZIE, 1986, 319 (06) :500-505

[12] ANTIPHLOGISTIC 2,3-DIHYDRO-1H-PYRROLIZINES .6. SODIUM PERIODATE-OXIDATION OF 2,3-DIHYDRO-6,7-DIPHENYL-1H-PYRROLIZINE [J].

DANNHARDT, G ;

STEINDL, L .

ARCHIV DER PHARMAZIE, 1985, 318 (07) :661-663

[13] Recent progress in asymmetric intermolecular C-H activation by rhodium carbenoid intermediates [J].

Davies, HML ;

Antoulinakis, EG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :47-55

[14] Catalytic asymmetric benzylic C-H activation by means of carbenoid-induced C-H insertions [J].

Davies, HML ;

Jin, QH ;

Ren, PD ;

Kovalevsky, AY .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4165-4169

[15]

Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO

[16]

2-6

[17] Synthetic studies on asperparaline A. Synthesis of the spirosuccinimide ring system [J].

Gonzalez, F ;

Sanz-Cervera, JF ;

Williams, RM .

TETRAHEDRON LETTERS, 1999, 40 (24) :4519-4522

[18]

Guari Y, 1999, EUR J INORG CHEM, P1047

[19] Direct carbonylation at a C-H bond in the benzene ring of 2-phenyloxazolines catalyzed by Ru3(CO)12.: Scope, limitations, and mechanistic aspects [J].

Ie, Y ;

Chatani, N ;

Ogo, T ;

Marshall, DR ;

Fukuyama, T ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1475-1488

[20]

Imhof W, 2001, ADV SYNTH CATAL, V343, P795, DOI 10.1002/1615-4169(20011231)343:8<795::AID-ADSC795>3.0.CO

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