Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with α,β-Unsaturated Ketones

被引：88

作者：

Hernandez-Toribio, Jorge ^{[1
]}

Gomez Arrayas, Ramon ^{[1
]}

Martin-Matute, Belen ^{[1
]}

Carretero, Juan C. ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 02期

关键词：

CHIRAL CALCIUM COMPLEXES; N-SULFONYL IMINES; PYRROLIDINE DERIVATIVES; EFFICIENT CATALYSTS; PROLINE DERIVATIVES; COPPER-COMPLEXES; ALKENES; LIGANDS; NITROALKENES;

D O I：

10.1021/ol802664m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha,beta-Unsaturated ketones are no longer the missing dipolarophiles in catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides. In the presence of Cu-1-Fesulphos complexes as catalysts (5 mol %), these substrates combine high reactivity, wide substitution tolerance, moderate to good endo/exo selectivities, and high enantiocontrol. The endo/exo-diastereoselectivity of the reaction is strongly dependent on the cis or trans nature of the enone moiety.

引用

页码：393 / 396

页数：4

共 38 条

[1] Asymmetric synthesis of an N-acylpyrrolidine for inhibition of HCV polymerase [J].

Agbodjan, Armel A. ;

Cooley, Bob E. ;

Copley, Royston C. B. ;

Corfield, John A. ;

Flanagan, Roy C. ;

Glover, Bobby N. ;

Guidetti, Rossella ;

Haigh, David ;

Howes, Peter D. ;

Jackson, Mary M. ;

Matsuoka, Richard T. ;

Medhurst, Katrina J. ;

Millar, Alan ;

Sharp, Matthew J. ;

Slater, Martin J. ;

Toczko, Jennifer F. ;

Xie, Shiping .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3094-3102

[2] Regio- and enantioselective synthesis of novel functionalized pyranopyrrolidines by 1,3-dipolar cycloaddition of carbohydrates [J].

Bashiardes, G ;

Cano, C ;

Mauzé, B .

SYNLETT, 2005, (04) :587-590

[3] Cationic planar chiral palladium PS complexes as highly efficient catalysts in the enantioselective ring opening of oxa- and azabicyclic alkenes [J].

Cabrera, S ;

Arrayás, RG ;

Carretero, JC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3944-3947

[4] Fesulphos-palladium(II) complexes as well-defined catalysts for enantioselective ring opening of meso heterobicyclic alkenes with organozinc reagents [J].

Cabrera, S ;

Arrayás, RG ;

Alonso, I ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17938-17947

[5] Highly enantioselective copper(I)-fesulphos-catalyzed 1,3-dipolar cycloaddition of azomethine ylides [J].

Cabrera, S ;

Arrayás, RG ;

Carretero, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16394-16395

[6] CuI-fesulphos complexes:: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides [J].

Cabrera, Silvia ;

Arrayas, Ramon Gomez ;

Martin-Matute, Belen ;

Cossio, Fernando P. ;

Carretero, Juan C. .

TETRAHEDRON, 2007, 63 (28) :6587-6602

[7] Asymmetric organocatalytic three-component 1,3-dipolar cycloaddition: Control of stereochemistry via a chiral bronsted acid activated dipole [J].

Chen, Xiao-Hua ;

Zhang, Wen-Quan ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5652-+

[8] New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions [J].

Dogan, Ozdemir ;

Koyuncu, Hasan ;

Garner, Philip ;

Bulut, Adnan ;

Youngs, Wiley J. ;

Panzner, Matthew .

ORGANIC LETTERS, 2006, 8 (21) :4687-4690

[9] Highly enantioselective asymmetric 1,3-dipolar cycloaddition of azomethine ylide catalyzed by a copper(I)/ClickFerrophos complex [J].

Fukuzawa, Shin-ichi ;

Oki, Hiroshi .

ORGANIC LETTERS, 2008, 10 (09) :1747-1750

[10] Catalytic asymmetric vinylogous Mannich reaction of N-(2-thienyl)sulfonylimines [J].

Gonzalez, Alvaro Salvador ;

Arrayas, Ramon Gomez ;

Rivero, Marta Rodriguez ;

Carretero, Juan C. .

ORGANIC LETTERS, 2008, 10 (19) :4335-4337

← 1 2 3 4 →