Abstract

Manganese-mediated radical addition reactions to chiral N-acylhydrazones produces amines with excellent stereocontrol, but prior work showed an incompatibility with aromatic N-heterocycles. Control reactions with various aromatic heterocycles as additives led to modified reaction conditions that permit improved radical additions to N-acylhydrazones in the presence of heteroaromatic compounds. The method was applied to a revised approach to tubuvaline utilizing radical addition to a chiral N-acylhydrazone bearing a thiazole moiety.

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