官能化异吲哚啉酮的合成：原位生成的有机铝试剂与酰亚胺离子的加成反应
Synthesis of Functionalized Isoindolinones: Addition of In Situ Generated Organoalanes to Acyliminium Ions.
作者信息
Pierce Joshua G, Waller David L, Wipf Peter
机构信息
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, U.S.A.
出版信息
J Organomet Chem. 2007 Oct 1;692(21):4618-4629. doi: 10.1016/j.jorganchem.2007.05.035.
Abstract
Addition of in situ generated di- or trisubstituted alkenylalanes to N-acyliminium ions provides rapid access to functionalized isoindolinones. Subsequent ring closing metathesis leads to tricyclic products. These transformations proceed under mild conditions and allow for the convergent synthesis of biologically significant scaffolds from readily available starting materials.
摘要
将原位生成的二取代或三取代链烯基丙氨酸添加到N-酰基亚胺离子中，可快速获得官能化异吲哚啉酮。随后的闭环复分解反应生成三环产物。这些转化在温和条件下进行，并且能够从易得的起始原料进行汇聚合成具有生物学意义的骨架。
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Org Lett. 2006 Aug 31;8(18):4101-4. doi: 10.1021/ol061614x.
2
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Org Lett. 2006 Jul 20;8(15):3375-8. doi: 10.1021/ol0613057.
3
Transition-metal-mediated cascade reactions: the water-accelerated carboalumination-Claisen rearrangement-carbonyl addition reaction.过渡金属介导的串联反应：水促进的碳铝化-克莱森重排-羰基加成反应
J Org Chem. 2005 Sep 30;70(20):8096-102. doi: 10.1021/jo051211v.
4
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5
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7
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