Selective Electron Transfer Reduction of Urea-Type Carbonyls

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Abstract

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.

Bibliographical metadata

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Early online date14 Jun 2018
DOIs
Publication statusPublished - 20 Aug 2018