Furan and pyrrole heterocycles are important structural motifs commonly found in natural products and pharmaceuticals. Trisubstituted furans carrying a single carbon unit in the C3 position are prevalent in a number of biologically active natural products and therefore of particular synthetic interest. We target these structures as part of a research program aimed at the <i>de novo</i> synthesis of functionalized heterocyclic compounds. Olefin metathesis reactions between readily available allylic alcohols or allylic amines and enones give rapid access to γ-hydroxyenones and γ-aminoenones which undergo photochemical aromatization under extraordinarily mild conditions. Similarly, trisubstituted furans can be obtained <i>via </i>temporary silicon-tethered olefin metathesis and subsequent photochemical aromatization of the corresponding substituted γ-hydroxyenones.

Photochemical aromatization: A novel approach to substituted furans and pyrroles under neutral conditions

253rd National Meeting (2017)

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