An expedient phosphine-catalyzed [4+2] annulation: Synthesis of highly functionalized tetrahydropyridines

被引：447

作者：

Zhu, XF ^{[1
]}

Lan, J ^{[1
]}

Kwon, O ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 16期

关键词：

D O I：

10.1021/ja0344009

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ethyl 2-methyl-2,3-butadienoate acts as a 1,4-dipole synthon and undergoes [4 + 2] annulation with N-tosylimines in the presence of an organic phosphine catalyst. The resulting adducts, ethyl 6-substituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates, are formed in excellent yields with complete regioselectivity. Mechanistic reasoning for this new annulation has led to an expansion of the reaction scope by employing ethyl 2-(substituted-methyl)-2,3-butadienoates to give ethyl 2,6-cis-disubstituted-1-(4-tosyl)-1,2,5,6-tetrahydro-pyridine-3-carboxylates with high diastereoselectivities. Copyright © 2003 American Chemical Society.

引用

页码：4716 / 4717

页数：2

共 33 条

[1] PREPARATION OF METHYL-2-(OMEGA-IODOALKYL)PROPENOATES AND A FACILE ROUTE TO 2-CARBOMETHOXY-1,3-BUTADIENE [J].

ALANINE, AID ;

FISHWICK, CWG ;

JONES, AD ;

MITCHELL, MB .

TETRAHEDRON LETTERS, 1989, 30 (41) :5653-5654

[2] Solid-supported synthesis of imidazoles: A strategy for direct resin-attachment to the imidazole core [J].

Bilodeau, MT ;

Cunningham, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2800-2801

[3]

Boger D. L., 1987, HETERO DIELS ALDER M

[4]

Chemla F, 2000, SYNTHESIS-STUTTGART, P75

[5]

Dewick P. M., 1997, MED NATURAL PRODUCTS

[6] Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition [J].

Du, YS ;

Lu, XY ;

Yu, YH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8901-8905

[7] The vinylogous intramolecular Morita-Baylis-Hillman reaction: Synthesis of functionalized cyclopentenes and cyclohexenes with trialkylphosphines as nucleophilic catalysts [J].

Frank, SA ;

Mergott, DJ ;

Roush, WR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) :2404-2405

[8]

HUISGEN R, 1969, TOPICS HETEROCYCLIC, pCH8

[9] NEW SYNTHESIS OF METHYL 1,3-BUTADIENE-2-CARBOXYLATE BY THE CHELETROPIC EXTRUSION OF CARBON-MONOXIDE FROM 3-CARBOMETHOXY-3,4-PENTADIENAL AND A STUDY OF ITS DIMERIZATION TO GIVE DIMETHYL MIKANECATE (DIMETHYL 4-ETHENYL-1-CYCLOHEXENE-1,4-DICARBOXYLATE) [J].

JUNG, ME ;

ZIMMERMAN, CN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7813-7814

[10] Novel phosphine-catalyzed zipper cyclization of aliphatic diyne-dione and yne-dione systems [J].

Kuroda, H ;

Tomita, I ;

Endo, T .

ORGANIC LETTERS, 2003, 5 (02) :129-131

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