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

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• 作者：Jorge Hernndez-Toribio ; Ramn Gmez Arrays ; Beln Martn-Matute ; Juan C. Carretero
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：January 15, 2009
• 年：2009
• 卷：11
• 期：2
• 页码：393-396
• 全文大小：175K
• 年卷期：v.11,no.2(January 15, 2009)
• ISSN：1523-7052

文摘

α,β-Unsaturated ketones are no longer the missing dipolarophiles in catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides. In the presence of Cu^I−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.