Frontispiece: The Brønsted Acid-Catalyzed, Enantioselective Aza-Diels-Alder Reaction for the Direct Synthesis of Chiral Piperidones

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• 作者：Dr. Claudia Weilbeer ; Dr. Marcel Sickert ; Dr. Sergei Naumov and Prof. Dr. Christoph Schneider
• 刊名：Chemistry - A European Journal
• 出版年：2017
• 出版时间：January 12, 2017
• 年：2017
• 卷：23
• 期：3
• 全文大小：1997K
• ISSN：1521-3765

文摘

The Rapid Assembly of Molecular Complexity…. …ranks among the most important challenges in modern organic chemistry. In their communication on page 513 ff., Schneider et al. have developed a 3-component, formal aza-Diels Alder reaction of aldehydes, para-anisidine, and a silyl dienolate which assembles a broad range of 2-piperidones in one synthetic step with excellent enantioselectivity when catalyzed by a chiral phosphoric acid. DFT-calculations of this process point to a stepwise mechanism comprising a domino-vinylogous Mannich lactamization reaction. The products were shown to be readily manipulated to furnish poly-alkylated piperidines. That strategy might prove highly useful in the context of stereoselective alkaloid synthesis.