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Synthesis 1994; 1994(10): 1083-1086
DOI: 10.1055/s-1994-25642
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Wittig-Horner Reaction of Dimethyl Phthalide-3-phosphonates with Ketones: Synthesis of 3-Ylidenephthalides and Their Conversion to 2,2-Disubstituted Indan-1,3-diones Including Spirocyclic Compounds

Mitsuaki Watanabe* , Hitoshi Morimoto, Maya Tomoda, Umeka Iwanaga
  • *Center for Instrumental Analysis, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852, Japan
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Publication Date:
27 September 2002 (online)

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The Wittig-Horner reaction of dimethyl phthalide-3-phosphonates with various ketones was investigated under the conditions: lithium bis(trimethylsilyl)amide (LHMDS) or sodium hydride in tetrahydrofuran, and cesium carbonate in isopropyl alcohol. The sequential treatment of the 3-ylidenephthalides with diisobutylaluminium hydride (DIBAL-H) and pyridinium dichromate (PDC) afforded 2,2-disubstituted indan-1,3-dione derivatives in modest to high overall yields.

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