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Jeremy Fournier, Dr. Oscar Lozano, Dr. Candice Menozzi, Dr. Stellios Arseniyadis and Prof. Dr. Janine Cossy Palladium-Catalyzed Asymmetric Allylic Alkylation of Cyclic Dienol Carbonates: Efficient Route to Enantioenriched γ-Butenolides Bearing an All-Carbon α-Quaternary Stereogenic Center Angewandte Chemie International Edition 52

Article first published online: 7 DEC 2012 | DOI: 10.1002/anie.201206368

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Alpha, beta, gamma: Allyl dienol carbonates (1) served as substrates for the title reaction to afford the furanones 2 in both high yields and high enantioselectivities. These furanones were eventually converted into valuable building blocks including γ-tertiary and γ-quaternary furanones (3) as well as β-quaternary butyrolactones (4). This method was used as a key step in the total synthesis of (−)-nephrosteranic acid and (−)-roccellaric acid.

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