An alkoxycarbonyl radical <i>5-exo</i> cyclization cross-coupling cascade has been developed that allows functionalized gamma-butyrolactones to be prepared in one step from simple tertiary-alcohol derived homoallylic oxalate precursors. The reaction succeeds with aryl and vinyl electrophiles and is compatible with heterocyclic fragments in both coupling partners. This chemistry allows for the rapid construction of spirolactones, which are of interest in drug discovery endeavors because of their rigid three-dimensional structures.

Facile preparation of spirolactones by an alkoxycarbonyl radical <i>5-exo </i>cyclization cross-coupling cascade

2019 Fall National Meeting

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Facile preparation of spirolactones by an alkoxycarbonyl radical 5-exo cyclization cross-coupling cascade