Diels-Alder Cycloaddition of Chiral Nonracemic 2,5-Diketopiperazine Dienes
Diels-Alder Cycloaddition of Chiral Nonracemic 2,5-Diketopiperazine Dienes
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DOI：
10.1021/ol201768f
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发表时间：
2011-08-19
期刊：
影响因子：
5.2
通讯作者：
Scheerer, Jonathan R.
中科院分区：
文献类型：
--
作者：
Morris, Erin N.;Nenninger, E. Katherine;Scheerer, Jonathan R.
手性非外消旋2，5-二酮哌嗪二烯的制备使分子间杂Diels-桤木环加成反应的研究成为可能。二酮哌嗪二烯与富电子和缺电子烯烃底物均具有反应性。环加成反应中的非对映体控制是通过一个可移动的缩醛胺取代基来实现的。本研究部分阐明了二酮哌嗪环加成反应的区域化学、立体电子学和反应性偏好，并提供了一种直接非对映选择性合成双环[2.2.2]二氮杂辛烷结构的途径。
Preparation of a chiral, nonracemic 2,5-diketopiperazine diene has enabled the Investigation of Intermolecular hetero-Diels-Alder cycloadditions. The diketopiperazine diene is reactive with both electron-rich and -deficient alkene substrates. Diastereofacial control In the cycloaddition Is enforced with a removable aminal substituent. This study partly illuminates the regiochemical, stereoelectronic, and reactivity preferences of the diketopiperazine cycloaddition as well as provides a direct diastereoselective synthetic route to bicyclo[2.2.2]diazaoctane structures.