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
收藏
页码：393 / 396
页数：4
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