Synthetic and Mechanistic Studies of the Aza-Retro-Claisen Rearrangement. A Facile Route to Medium Ring Nitrogen Heterocycles

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• 作者：Robert K. Boeckman ; Jr. ; Nathan E. Genung ; Ke Chen ; Todd R. Ryder
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：April 2, 2010
• 年：2010
• 卷：12
• 期：7
• 页码：1628-1631
• 全文大小：230K
• 年卷期：v.12,no.7(April 2, 2010)
• ISSN：1523-7052

文摘

An efficient synthesis of medium-sized heterocyclic rings was achieved using a one-pot aza-Wittig/retro-aza-Claisen sequence of vinyl cyclobutanecarboxaldehydes derived from simple allylic carbonates. The use of various Staudinger reagents in the aza-Wittig reaction allows for a variety of N-substituted products to be obtained. The rearrangement is under thermodynamic control driven by relief of the cyclobutane ring strain and resonance stabilization of the resulting vinylogous amide/sulfonamide.