Catalytic imino Diels-Alder reaction by triflic imide and its application to one-pot synthesis from three components

被引：59

作者：

Takasu, Kiyosei ^{[1
]}

Shindoh, Naoya ^{[1
]}

Tokuyama, Hidetoshi ^{[1
]}

Ihara, Masataka ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON | 2006年 / 62卷 / 51期

关键词：

imino Diels-Alder reaction; substituted piperidines; triflic imide; three component reaction;

D O I：

10.1016/j.tet.2006.09.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An imino Diels-Alder reaction of 2-siloxydienes with aldimines catalyzed by triflic imide (Tf2NH; 0.1 similar to 10 mol % amount) has been developed leading to substituted piperidin-4-ones. Tf2NH catalyst is compatible with basic functions, such as pyridine and indole rings in the imino Diels-Alder reaction. Furthermore, X-ray crystallographic analysis indicates that trans-2,6-diphenyl-4-piperidinone 4a obtained by this reaction has a unique conformation in the solid state. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：11900 / 11907

页数：8

共 34 条

[1] AKIBA KY, 1993, SYNLETT, P657
[2] Bronsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media
Akiyama, T
Takaya, J
Kagoshima, H
[J]. TETRAHEDRON LETTERS, 1999, 40 (44) : 7831 - 7834
[3] Synthesis and in vitro microbiological evaluation of imidazo(4,5-b)pyridinylethoxypiperidones
Aridoss, G
Balasubramanian, S
Parthiban, P
Kabilan, S
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (02) : 268 - 275
[4] ATHMAN RB, 2005, ORG LETT, V7, P5335
[5] Study of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky's diene.
Badorrey, R
Cativiela, C
Díaz-de-Villegas, MD
Gálvez, JA
[J]. TETRAHEDRON, 1999, 55 (24) : 7601 - 7612
[6] Catalytic imino-Diels-Alder reactions of 2-aminodienes:: a simple entry into structurally diverse pipecolic acid derivatives
Barluenga, J
Fernández, MA
Aznar, F
Valdés, C
[J]. TETRAHEDRON LETTERS, 2002, 43 (45) : 8159 - 8163
[7] Boger D. L., 1987, HETERO DIELS ALDER M
[8] Tris(trimethylsilyl)silyl-governed aldehyde cross-aldol cascade reaction
Boxer, MB
Yamamoto, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) : 48 - 49
[9] Recent developments in imino Diels-Alder reactions
Buonora, P
Olsen, JC
Oh, T
[J]. TETRAHEDRON, 2001, 57 (29) : 6099 - 6138
[10] USEFUL DIENE FOR DIELS-ALDER REACTION
DANISHEFSKY, S
KITAHARA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) : 7807 - 7808

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