New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems.
New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems.
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DOI：
10.1021/acs.chemrev.9b00481
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发表时间：
2020-03-11
期刊：
影响因子：
62.1
通讯作者：
Zanardi F
中科院分区：
文献类型：
--
作者：
Curti C;Battistini L;Sartori A;Zanardi F
葡萄学原理表明，分子中官能团的电子效应可能通过插入的共轭多键传递到远端位置。作为一个典型的例子，π扩展烯醇酸型链体系的亲核特性可能从合法的α-位点传递到葡萄状的γ， ε，…如果采用合适的homo提升策略，可以将不饱和亲核原前体转化为反应性多烯酸酯类。另一方面，当“非天然”羰基ipso位点被激活为亲核试剂（umpolung）时，乙烯基化将亲核特性扩展到“非天然”β, δ，…远程站点。将葡萄酒学原理与活化模式和概念相结合，如铝离子/烯胺有机催化、nhc -有机催化、有机/金属协同催化、双功能有机催化、二氰烷基烷活化和有机级联反应，代表了所有葡萄酒学转化的一个令人印象深刻的进步。这篇综述文章通过收集、比较和批判性地描述2010-2018年9年间在葡萄酸烯醇酸型供体底物的产生及其在化学合成中的应用方面取得的成就，来庆祝这一进化进展。
The principle of vinylogy states that the electronic effects of a functional group in a molecule are possibly transmitted to a distal position through interposed conjugated multiple bonds. As an emblematic case, the nucleophilic character of a π-extended enolate-type chain system may be relayed from the legitimate α-site to the vinylogous γ, ε, ..., ω remote carbon sites along the chain, provided that suitable HOMO-raising strategies are adopted to transform the unsaturated pronucleophilic precursors into the reactive polyenolate species. On the other hand, when “unnatural” carbonyl ipso-sites are activated as nucleophiles (umpolung), vinylogation extends the nucleophilic character to “unnatural” β, δ, ... remote sites. Merging the principle of vinylogy with activation modalities and concepts such as iminium ion/enamine organocatalysis, NHC-organocatalysis, cooperative organo/metal catalysis, bifunctional organocatalysis, dicyanoalkylidene activation, and organocascade reactions represents an impressive step forward for all vinylogous transformations. This review article celebrates this evolutionary progress, by collecting, comparing, and critically describing the achievements made over the nine year period 2010–2018, in the generation of vinylogous enolate-type donor substrates and their use in chemical synthesis.
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影响因子：
2.1
作者：
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