The Emergence of Quinone Methides in Asymmetric Organocatalysis.
The Emergence of Quinone Methides in Asymmetric Organocatalysis.
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DOI：
10.3390/molecules200711733
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发表时间：
2015-06-25
期刊：
影响因子：
--
通讯作者：
Bernardi L
中科院分区：
文献类型：
--
作者：
Caruana L;Fochi M;Bernardi L
醌类化合物（QMs）是一种高活性化合物，在有机化学中被定义为“难以捉摸的”中间体，甚至是一个“合成谜”。事实上，直到几年前，它们在催化不对称环境中的应用只有少数几个例子。本综述收集了使用QM作为底物和中间体的有机催化不对称反应，从早期的例子（主要基于具有特定取代模式的稳定QM）到最近的贡献，这些贡献极大地扩展了QM化学的范围。事实上，直到最近才实现了通过与有机催化方法相容的策略在原位生成QMs。这种策略最终为充分利用这些不稳定的中间体打开了大门，导致了一系列引人注目的披露。几种类型的合成强大的不对称加成和环加成反应，适用于广泛的QMs，现在是可用的。
Quinone methides (QMs) are highly reactive compounds that have been defined as “elusive” intermediates, or even as a “synthetic enigma” in organic chemistry. Indeed, there were just a handful of examples of their utilization in catalytic asymmetric settings until some years ago. This review collects organocatalytic asymmetric reactions that employ QMs as substrates and intermediates, from the early examples, mostly based on stabilized QMs bearing specific substitution patterns, to more recent contributions, which have dramatically expanded the scope of QM chemistry. In fact, it was only very recently that the generation of QMs in situ through strategies compatible with organocatalytic methodologies has been realized. This tactic has finally opened the gate to the full exploitation of these unstable intermediates, leading to a series of remarkable disclosures. Several types of synthetically powerful asymmetric addition and cycloaddition reactions, applicable to a broad range of QMs, are now available.
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影响因子：
18.3
作者：
Bai, Wen-Ju;David, Jonathan G.;Feng, Zhen-Gao;Weaver, Marisa G.;Wu, Kun-Liang;Pettus, Thomas R. R.
通讯作者：
Pettus, Thomas R. R.
影响因子：
16.6
作者：
El-Sepelgy, Osama;Haseloff, Stefan;Schneider, Christoph
通讯作者：
Schneider, Christoph
DOI：
10.1039/c29710000383
发表时间：
1971-01-01
期刊：
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS
影响因子：
--
作者：
CHAPMAN, OL;MCINTOSH, CL
通讯作者：
MCINTOSH, CL
影响因子：
16.6
作者：
Chu, Wen-Dao;Zhang, Le-Fen;Fan, Chun-An
通讯作者：
Fan, Chun-An
影响因子：
3.9
作者：
Gharpure, Santosh J.;Sathiyanarayanan, A. M.;Vuram, Prasanna K.
通讯作者：
Vuram, Prasanna K.