Dienamine-Catalyzed Nitrone Formation via Redox Reaction
Dienamine-Catalyzed Nitrone Formation via Redox Reaction
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DOI：
10.1021/acs.orglett.6b00770
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发表时间：
2016-05-06
期刊：
影响因子：
5.2
通讯作者：
Brenner-Moyer, Stacey E.
中科院分区：
文献类型：
--
作者：
Fraboni, Americo J.;Brenner-Moyer, Stacey E.
第一个催化方法直接引入硝酮功能醛基板上进行说明。该反应通过前所未有的有机催化氧化还原机制进行，其中烯醛通过二烯胺催化氧化为γ-硝酮，从而还原一当量的亚硝基苯。该反应是烯醛的发散反应性的一个独特的例子，其代表了用于快速访问N，O-杂环的小文库的新策略。或者，可以简单地通过改变溶剂来抑制发散反应性。
The first catalytic method to directly introduce nitrone functionality onto aldehyde substrates is described. This reaction proceeds by an unprecedented organocatalytic redox mechanism in which an enal is oxidized to the gamma-nitrone via dienamine catalysis, thereby reducing an equivalent of nitrosobenzene. This reaction is a unique example of divergent reactivity of an enal, which represents a novel strategy for rapidly accessing small libraries of N,O-heterocycles. Alternatively, divergent reactivity can be suppressed simply by changing solvents.