银离子诱导的γ-氨基碘代物的Grob 碎裂反应：多取代哌啶的高立体选择性合成。
Silver ion-induced Grob fragmentation of gamma-amino iodides: highly stereoselective synthesis of polysubstituted piperidines.
机构信息
Departement de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
出版信息
Org Lett. 2008 Dec 4;10(23):5497-9. doi: 10.1021/ol8024605.
PMID:19006316
Abstract
A new concerted silver ion-mediated Grob fragmentation process is described in which a 1,2-dihydropyridinium ion is formed and trapped in situ with Grignard reagents in a highly regio- and diastereoselective fashion. Using this methodology, 2,3,6-trisubstituted piperidines were synthesized in good yields and further derivatized to polysubstituted indolizidine.
摘要
描述了一种新的协同银离子介导的Grob 重排反应过程，其中 1,2-二氢吡啶鎓离子在格氏试剂的存在下以高度区域和立体选择性的方式原位形成并捕获。使用该方法，以良好的收率合成了 2,3,6-三取代的哌啶，并进一步衍生为多取代的吲哚里西定。
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