Selective Catalytic Monoreduction of Phthalimides and Imidazolidine-2,4-diones
Selective Catalytic Monoreduction of Phthalimides and Imidazolidine-2,4-diones
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DOI：
10.1002/anie.201104226
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发表时间：
2011-01-01
影响因子：
16.6
通讯作者：
Beller, Matthias
中科院分区：
文献类型：
--
作者：
Das, Shoubhik;Addis, Daniele;Beller, Matthias
异吲哚啉酮因其广泛而多样的生物活性而成为有机合成的一个有吸引力的目标，也是药物化学的一个有价值的支架（方案1）。[1-3]尽管有许多已知的方法，但人们对开发合成这些化合物的方便和通用的方案一直感兴趣。因此，近年来，新的方法如铼催化芳香醛亚胺与异氰酸酯的反应，[4a]酸催化的氮杂-纳扎罗夫反应N-酰基亚胺离子[4b]钯催化的苄胺羰基化[4c]和α-取代的2-乙烯基苯甲酰胺[4d]的碘胺化已得到开发。尽管取得了所有这些成就，现成的邻苯二甲酰亚胺的选择性单还原代表了获得此类化合物的最直接和有效的途径。已知的邻苯二甲酰亚胺的还原反应在酸存在下使用化学计量的锡[5]或锌[6]。另一方面，更常见的有机金属氢化物的应用，
Isoindolinones represent an attractive target for organic synthesis and a valuable scaffold for medicinal chemistry because of their widespread and diverse biological activities (Scheme 1).[1–3] Despite many known methods, there is an ongoing interest in the development of convenient and general protocols for the synthesis of these compounds.Hence, in recent years, novel approaches such as rheniumcatalyzed reactions of aromatic aldimines with isocyanates,[4a] acid-catalyzed aza-Nazarov reactions of N-acyliminium ions,[4b] palladium-catalyzed carbonylations of benzylic amines,[4c] and iodoaminations of α-substituted 2-vinylbenzamides [4d] have been developed. In spite of all these achievements, the selective monoreduction of readily available phthalimides represents the most straightforward and efficient route to this class of compounds. Known reductions of phthalimides make use of stoichiometric amounts of tin [5] or zinc [6] in the presence of an acid. On the other hand, the application of more common organometallic hydrides, for