Intriguing Behavior of Cinchona Alkaloids in the Enantioselective Organocatalytic Hydroxyamination of -Substituted-<img src="http://

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• 作者：Jesú ; s Ló ; pez-Cantarero ; M. Belé ; n Cid ; Thomas B. Poulsen ; Marco Bella ; José ; Luis Garcí ; a Ruano ; Karl Anker J<img src="http ; //pubs.acs.org/images/gifchars/oslash.gif" bor
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：August 31, 2007
• 年：2007
• 卷：72
• 期：18
• 页码：7062 - 7065
• 全文大小：83K
• 年卷期：v.72,no.18(August 31, 2007)
• ISSN：1520-6904

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The cinchona alkaloid quinine promotes the enantioselectivenitroso-aldol reaction between -aryl--cyanoacetates andnitrosobenzene to give the hydroxyamination products withtotal chemoselectivity. Treatment of the reaction mixture withZn/AcOH affords the corresponding amines in high yieldand moderate enantioselectivity. An unusual effect on theenantioselectivity was observed with the catalyst loading andsolvent. A reductive protocol allows the construction of anoptically active 1,2-diamine moiety bearing a quaternarycenter.