The direct addition of pyridine and diazine units to electron-poor alkenes has been achieved <i>via</i> a redox radical mechanism that is enabled by limiting the effective concentration of the hydrogen-atom source. The described method is tolerant of acidic functional groups and is generally applicable to the union of a wide range of Michael acceptors and 6-membered heterocyclic halides. This method has been advanced to the preparation of unnatural amino acids via conjugate addition of heteroaryl- and alkyl radicals (generated from a number of different precursors) to dehydroalanine derivatives. The use of tertiary amines in this system results in α-amino radical conjugate addition to dehydroalanine with high fidelity. This reactivity is applicable to the conjugate addition of radicals generated from highly complex amine-containing structures and enables their conjugation to dehydroalanine peptides.<br/>

Radical conjugate addition of N-heterocycles and tertiary amines

2019 Fall National Meeting

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