Flexible Stereoselective Functionalizations of Ketones through Umpolung with Hypervalent Iodine Reagents
Flexible Stereoselective Functionalizations of Ketones through Umpolung with Hypervalent Iodine Reagents
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DOI：
10.1002/anie.201400405
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发表时间：
2014-06-01
影响因子：
16.6
通讯作者：
Wirth, Thomas
中科院分区：
文献类型：
--
作者：
Mizar, Pushpak;Wirth, Thomas
羰基化合物在α位置的功能化作为一种合成途径受到了广泛的关注，因为这类产物具有广泛的生物学意义。通过极性反转或“极性翻转”，我们在这里展示了典型的亲核试剂，如氧、氮，甚至碳亲核试剂，在将它们拴在烯醇醚上后，可以用于加成反应。我们的发现允许新的反合成规划和快速组装的结构，以前只能通过多步序列。
The functionalization of carbonyl compounds in the alpha-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or "umpolung", we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences.