An Asymmetric Synthesis of (2S,5S)-5-Substituted Azepane-2-Carboxylate Derivatives

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• 作者：Donn G. Wishka ; Marion Be虂dard ; Katherine E. Brighty ; Richard A. Buzon ; Kathleen A. Farley ; Michael W. Fichtner ; Goss S. Kauffman ; Jaap Kooistra ; Jason G. Lewis ; Hardwin O鈥橠owd ; Ivan J. Samardjiev ; Brian Samas ; Geeta Yalamanchi ; Mark C. Noe
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：March 18, 2011
• 年：2011
• 卷：76
• 期：6
• 页码：1937-1940
• 全文大小：752K
• 年卷期：v.76,no.6(March 18, 2011)
• ISSN：1520-6904

文摘

To facilitate a drug discovery project, we needed to develop a robust asymmetric synthesis of (2S,5S)-5-substituted-azepane-2-carboxylate derivatives. Two key requirements for the synthesis were flexibility for elaboration at C5 and suitability for large scale preparation. To this end we have successfully developed a scalable asymmetric synthesis of these derivatives that starts with known hydroxy-ketone 8. The key step features an oxidative cleavage of aza-bicyclo[3.2.2]nonene 14, which simultaneously generates the C2 and C5 substituents in a stereoselective manner.