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A Facile Approach to the Synthesis of Allylic Spiro Ethers and Lactones

Ming-Chang P. Yeh*, Yi-Chin Lee, Tsao-Ching Young

*Department of Chemistry, National Taiwan Normal University, Taipei 117, Taiwan, Email: cheyehscc.ntnu.edu.tw

M.-C. P. Yeh, Y.-C. Lee, T.-C. Young, Synthesis, 2006, 3621-3624.

DOI: 10.1055/s-2006-950294


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Abstract

Treatment of 3-[(alkoxycarbonyl)alkyl]-substituted conjugated cycloalkenones with diisobutylaluminum hydride at -78 C followed by acid quenching furnishes spiro ethers, whereas the corresponding 3-(carboxyalkyl)-substituted cycloalkenones generate spiro lactones upon reaction with sodium borohydride at 30 C followed by acid quenching.

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Key Words

enones, cyclic ethers, lactones, spiro compounds, Luche reduction, DIBAL-H, sodium borohydride


ID: J66-Y2006-3630