Reaction Discovery Employing Macrocycles: Transannular Cyclizations of Macrocyclic Bis-lactams

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• 作者：Chong Han ; Sathish Rangarajan ; Alicia C Voukides ; Aaron B. Beeler ; Richard Johnson ; John A. Porco
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：January 15, 2009
• 年：2009
• 卷：11
• 期：2
• 页码：413-416
• 全文大小：220K
• 年卷期：v.11,no.2(January 15, 2009)
• ISSN：1523-7052

文摘

Macrocyclic bis-lactams have been synthesized by cyclodimerization of homoallylic amino esters employing a Zr(IV)-catalyzed ester-amide exchange protocol. Base-mediated transannular cyclizations have been identified to access both bicyclic [5-11] and tricyclic [5-8-5] frameworks in good yield and diastereoselectivity. Preliminary mechanistic studies support an olefin isomerization−intramolecular conjugate addition pathway.