Reaction Discovery Employing Macrocycles: Transannular Cyclizations of Macrocyclic Bis-lactams
Reaction Discovery Employing Macrocycles: Transannular Cyclizations of Macrocyclic Bis-lactams
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DOI：
10.1021/ol802729f
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发表时间：
2009-01-15
期刊：
影响因子：
5.2
通讯作者：
Porco, John A., Jr.
中科院分区：
文献类型：
--
作者：
Han, Chong;Rangarajan, Sathish;Porco, John A., Jr.
大环双内酰胺是通过采用 Zr(IV) 催化的酯-酰胺交换方案对同烯丙基氨基酯进行环二聚而合成的。碱基介导的跨环环化已被确定能够以良好的产率和非对映选择性获得双环[5-11]和三环[5-8-5]框架。初步机理研究支持烯烃异构化-分子内共轭加成途径。
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.