酰胺的反烯反应的化学选择性α-氘代
Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction.
机构信息
Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Vienna, Austria.
CeMM-Research Center for Molecular Medicine, Austrian Academy of Sciences, Lazarettgasse 14, AKH BT 25.3, 1090, Vienna, Austria.
出版信息
Chemistry. 2020 Dec 1;26(67):15509-15512. doi: 10.1002/chem.202004103. Epub 2020 Nov 17.
A synthetically convenient approach for the direct α-deuteration of amides is reported. This mechanistically unusual process relies on a retro-ene-type process, triggered by the addition of deuterated dimethyl sulfoxide to a keteniminium intermediate, generated through electrophilic amide activation. The transformation displays broad functional-group tolerance and high deuterium incorporation.
本文报道了一种酰胺直接α-氘代的合成方法。这种机制不同寻常的过程依赖于-retro-ene-型过程，通过亲电酰胺活化生成的烯酮亚胺中间体与氘代二甲亚砜加成触发。该转化具有广泛的官能团耐受性和高氘掺入。
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