Imino-Diels-Alder and imino-aldol reactions catalyzed by samarium diiodide

被引：52

作者：

Collin, J ^{[1
]}

Jaber, N ^{[1
]}

Lannou, MI ^{[1
]}

机构：

[1] Univ Paris Sud, ICMO, Lab Catalyse Mol, ESA 8075, F-91405 Orsay, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 42期

关键词：

samarium diiodide; catalysis; cycloadditions; imines; aldol reaction;

D O I：

10.1016/S0040-4039(01)01581-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence or a catalytic amount of samarium diiodide in methylene chloride, aromatic imines react with Danishefsky diene to form tetrahydropyridine-4-ones in high yields. Under the same conditions, various imino-aldol reactions afford beta -amino esters or beta -amino ketones. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：7405 / 7407

页数：3

共 20 条

[1] Chemoselective activation of aldimine in preference to aldehyde by the combination of BF3•OEt2 and water:: Novel catalyst for the Mannich-type reaction [J].

Akiyama, T ;

Takaya, J ;

Kagoshima, H .

CHEMISTRY LETTERS, 1999, (09) :947-948

[2] Indium triflate - An efficient catalyst for hetero Diels-Alder reactions [J].

Ali, T ;

Chauhan, KK ;

Frost, CG .

TETRAHEDRON LETTERS, 1999, 40 (30) :5621-5624

[3] Indium trichloride (InCl3)catalyzed imino Diels-Alder reactions:: An efficient synthesis of cyclopentaquinolines, azabicyclooctanones and azabicyclononanones. [J].

Babu, G ;

Perumal, PT .

TETRAHEDRON, 1998, 54 (08) :1627-1638

[4] Lanthanide iodides, a new family of efficient Lewis acid catalysts [J].

Collin, J ;

Giuseppone, N ;

Van de Weghe, P .

COORDINATION CHEMISTRY REVIEWS, 1998, 178 :117-144

[5] Tandem Mukaiyama Michael-aldol reactions catalyzed by samarium diiodide [J].

Giuseppone, N ;

Courtaux, Y ;

Collin, J .

TETRAHEDRON LETTERS, 1998, 39 (43) :7845-7848

[6] Mukaiyama aldol and Michael reactions catalyzed by lanthanide iodides [J].

Giuseppone, N ;

Van de Weghe, P ;

Mellah, M ;

Collin, J .

TETRAHEDRON, 1998, 54 (43) :13129-13148

[7] Enantioselective Diels-Alder reactions catalyzed by samarium iodo binaphthoxides [J].

Giuseppone, N ;

Santos, I ;

Collin, J .

TETRAHEDRON LETTERS, 2000, 41 (05) :639-642

[8]

GIUSEPPONE N, IN PRESS TETRAHEDRON

[9]

Hayakawa R, 1999, CHEM LETT, P591

[10]

ISHIHARA K, 1994, SYNLETT, P963

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