Rhodium(I)-catalysed hydrocarbonylation and silylcarbonylation reactions of alkynes in the presence of primary amines leading to 2-pyrrolidinones and 4-silylated 1-aza-1,3-butadienes

被引：29

作者：

Bärfacker, L ^{[1
]}

Hollmann, C ^{[1
]}

Eilbracht, P ^{[1
]}

机构：

[1] Univ Dortmund, Dept Chem, D-44221 Dortmund, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 18期

关键词：

D O I：

10.1016/S0040-4020(98)00160-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh(I)-catalysed hydrocarbonylation of alkynes 1 in the presence of primary amines gives substituted 2-pyrrolidinones 3 in a one-pot procedure. Replacement of hydrogen by hydrosilanes via silylcarbonylation leads to 4-silylated 1-aza-1,3-butadienes 5. These azadienes are converted with dimethyl acetylenedicarboxylate to 1,4-dihydropyridines 8 via Diels-Alder reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4493 / 4506

页数：14

共 40 条

[1] TICL4-MEDIATED REACTIONS OF ALKYL AZIDES WITH CYCLIC-KETONES
AUBE, J
MILLIGAN, GL
MOSSMAN, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) : 1635 - 1637
[2] CARBON-MONOXIDE AS A BUILDING-BLOCK IN ORGANIC-SYNTHESIS .4. DIRECT PREPARATION OF AMINES FROM ALKENES BY AMINOMETHYLATION CATALYZED BY DINUCLEAR RHODIUM COMPLEXES
BAIG, T
MOLINIER, J
KALCK, P
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 455 (1-2) : 219 - 224
[3] PROGRESS IN HYDROFORMYLATION AND CARBONYLATION
BELLER, M
CORNILS, B
FROHNING, CD
KOHLPAINTNER, CW
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) : 17 - 85
[4] Synthesis of 3-phenyl- and 5-phenyl-2-pyrrolidinone via rhodium catalysed carbonylation of allylamines.
Bertozzi, S
Salvadori, P
[J]. SYNTHETIC COMMUNICATIONS, 1996, 26 (16) : 2959 - 2965
[5] Chatani N, 1996, SYNLETT, P414
[6] INTRAMOLECULAR DIELS-ALDER ADDITIONS .1. ADDITIONS TO ANTHRACENE AND ACRIDINE
CIGANEK, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (08) : 1497 - 1505
[7] Cornils B., 1980, NEW SYNTHESES CARBON, P1
[8] HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE SILYLFORMYLATION OF ALKYNES UNDER MILD CONDITIONS PROMOTED BY DIRHODIUM(II) PERFLUOROBUTYRATE
DOYLE, MP
SHANKLIN, MS
[J]. ORGANOMETALLICS, 1994, 13 (04) : 1081 - 1088
[9] HIGHLY EFFICIENT REGIOSELECTIVE SILYLCARBONYLATION OF ALKYNES CATALYZED BY DIRHODIUM(II) PERFLUOROBUTYRATE
DOYLE, MP
SHANKLIN, MS
[J]. ORGANOMETALLICS, 1993, 12 (01) : 11 - 12
[10] SYNTHESIS OF PYRROLIZIDINE ALKALOIDS VIA RHODIUM-CATALYZED SILYLFORMYLATION AND AMIDOCARBONYLATION
EGUCHI, M
ZENG, QP
KORDA, A
OJIMA, I
[J]. TETRAHEDRON LETTERS, 1993, 34 (06) : 915 - 918

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