Through an efficient one-pot reaction sequence, ethyl propiolate can be transformed into a complex, usefully functionalized bicyclic product. Thioconjugate addition has been developed for both aromatic thiols (trialkylamine-catalyzed) and aliphatic thiols (KOtBu-catalyzed). Oxidation to sulfones and Li-catalyzed Diels�Alder cycloaddition complete the sequence with useful product yields. These subsequent steps are performed in situ, without any purification of intermediates.

One-pot three-step conjugate addition-oxidation-Diels–Alder reactions of ethyl propiolate

244th National Meeting (2012)

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