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

被引：87

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

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