NHC-Catalyzed Generation of α,β-Unsaturated Acylazoliums for the Enantioselective Synthesis of Heterocycles and Carbocycles,Accounts of Chemical Research

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NHC-Catalyzed Generation of α,β-Unsaturated Acylazoliums for the Enantioselective Synthesis of Heterocycles and Carbocycles
Accounts of Chemical Research ( IF 16.4 ) Pub Date : 2019-01-17 00:00:00 , DOI: 10.1021/acs.accounts.8b00550
Santigopal Mondal ₁ , Santhivardhana Reddy Yetra ₁ , Subrata Mukherjee ₁ , Akkattu T. Biju ₂

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This Account is aimed at highlighting the recent developments in the N-heterocyclic carbene (NHC)-catalyzed generation of α,β-unsaturated acylazolium intermediates and their subsequent reactivity with (bis)nucleophiles thereby shedding light on the power of this NHC-bound intermediate in organocatalysis. This key intermediate can be generated by the addition of NHCs to α,β-unsaturated aldehyde or acid derivatives. A wide variety of bisnucleophiles can add across the α,β-unsaturated acylazoliums to form various five and six-membered heterocycles and carbocycles. Moreover, suitably substituted nucleophiles can add to this intermediate and result in valuable products following cascade processes. Employing chiral NHCs in the process can result in the enantioselective synthesis of valuable compounds.

中文翻译：

NHC催化生成的α，β-不饱和酰基偶氮化合物用于杂环和碳环化合物的对映选择性合成

该报告旨在强调N杂环卡宾（NHC）催化生成的α，β-不饱和酰基zo中间体的最新进展及其与（双）亲核试剂的反应性，从而阐明这种与NHC结合的中间体的功能在有机催化中。该关键中间体可通过将NHC加到α，β-不饱和醛或酸衍生物中来生成。各种各样的双亲核试剂可以在α，β-不饱和酰基上加成，形成各种五元和六元杂环和碳环。而且，适当取代的亲核试剂可以添加到该中间体中，并在级联过程后产生有价值的产物。在此过程中使用手性NHC可导致有价值化合物的对映选择性合成。

更新日期：2019-01-17

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