Difunctionalization of readily accessible alkenes provides rapid access to a variety of complex motifs. However, controlling the regioselectivity of adding across alkenes remains a synthetic challenge. In our lab, we have developed a radical-relay strategy for the selective amino-functionalization of allylic alcohols via an imidate chaperone. Using photocatalytic conditions to initiate the generation of an imidate radical, this N-centered radical along with a hydrogen atom donor efficiently achieves hydroaminations of unbiased alkenes to selectively access 1,2-amino alcohols. These 1,2-amino alcohols are privileged motifs prevalent in biologically active compounds and in ligands and chiral auxiliaries used for synthetic transformations. To further expand upon this methodology, we have also developed an amino-alkylation and amino-arylation of allylic alcohols using novel radical traps to form C-N and C-C bonds in a single transformation. The synthetic utility and our mechanistic investigations will also be presented.<br/>

Selective radical-mediated amino-functionalization of allylic alcohols

256th National Meeting (2018)

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