Catalytic Asymmetric Total Syntheses of Quinine and Quinidine

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• 作者：Izzat T. Raheem ; Steven N. Goodman ; and Eric N. Jacobsen
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：January 28, 2004
• 年：2004
• 卷：126
• 期：3
• 页码：706 - 707
• 全文大小：61K
• 年卷期：v.126,no.3(January 28, 2004)
• ISSN：1520-5126

文摘

The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen(Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high selectivity.