Organocatalytic Michael Cycloisomerization of Bis(enones): The Intramolecular Rauhut−Currier Reaction

2002/02/26 by Long-Cheng Wang, Ana Liza Luis, Kyriacos Agapiou +2 · 5 citations
Chemistry · Medicine · #Advanced Synthetic Organic Chemistry #Asymmetric Synthesis and Catalysis #Microbial Natural Products and Biosynthesis

paper · doi:10.1021/ja0121686

openalex publication_date 2002/02/26 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

The utilization of enones as latent enolates enables regioselective enolate formation from chemically robust presursors. In this communication, we report a catalytic Michael cycloisomerization of bis(enones) under Morita-Baylis-Hillman conditions. Upon exposure to 10 mol % tributylphosphine, bis(enone) substrates afford both five- and six-membered ring products. Notably, unsymmetrical bis(enones) possessing sufficient steric or electronic bias yield single isomeric products.

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