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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Light-induced radical addition to oximes: a general route to branched primary amines
Zakhar M Rubanov1, Vitalij V Levin1, Alexander D Dilman1
1N. D. Zelinsky Institute of Organic Chemistry Leninsky Prosp. 47 119991 Moscow Russian Federation adil25@mail.ru.
Abstract:
A platform for the synthesis of branched primary amines via radical addition to unprotected oximes is described. Readily available alkyl iodides, alkanes, and carboxylic acids were used as radical precursors through XAT, HAT, and LMCT activation modes. The key feature is the use of a Brønsted acid to activate the radical addition step and to suppress side reactions. This approach is suitable for one-pot carbonyl alkylative amination, a transformation that was previously unavailable for the synthesis of primary amines.
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