Selective Electron Transfer Reduction of Urea‐Type Carbonyls,European Journal of Organic Chemistry

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Selective Electron Transfer Reduction of Urea‐Type Carbonyls
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2018-08-20 , DOI: 10.1002/ejoc.201800794
Huan-Ming Huang ₁ , David J. Procter ₁

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Urea‐type carbonyls in barbiturates undergo a highly chemoselective electron transfer reduction upon treatment with SmI₂/H₂O/LiBr. The process involves the formation, and further reduction, of unusual ketyl‐type radical anions under mild conditions. Cyclic aminal products are obtained in good to excellent yield without recourse to preactivation of the substrate or the use of metal hydride reagents. Furthermore, varying the protic additive used in conjunction with SmI₂ allows intermediate hemiaminals to be obtained.

中文翻译：

尿素型羰基的选择性电子转移还原

用SmI ₂ / H ₂ O / LiBr处理后，巴比妥酸酯中的尿素型羰基会发生高度化学选择性的电子转移还原。该过程涉及在温和条件下形成并进一步还原异常的酮基型自由基阴离子。以良好或优异的收率获得环状的氨基产物，而无需借助底物的预活化或使用金属氢化物试剂。此外，改变与SmI ₂结合使用的质子添加剂允许获得中等的血红蛋白。

更新日期：2018-09-17

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