Nitrile Ylides: Diastereoselective Cycloadditions using Chiral Oxzolidinones Without Lewis Acid

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• 作者：Mukund P. Sibi ; Takahiro Soeta ; Craig P. Jasperse
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：December 3, 2009
• 年：2009
• 卷：11
• 期：23
• 页码：5366-5369
• 全文大小：198K
• 年卷期：v.11,no.23(December 3, 2009)
• ISSN：1523-7052

文摘

Lewis acid complexation is generally required for chiral-auxiliary-controlled stereoselectivity, and chiral Lewis acid catalysis is frequently optimal for introducing asymmetry. In this work, we show that nitrile ylide cycloadditions to electron-poor acceptors attached to chiral auxiliaries proceed in high yield and stereoselectivity in the absence of Lewis acids. In contrast, chiral Lewis acids are inferior in these cycloadditions.