A Novel Synthesis of Bicyclic Isoxazolines via Sequential Michael and Intramolecular 1,3-Dipolar Additions

Hidemitsu Uno; Noriko Watanabe; Satomi Fujiki; Hitomi Suzuki

doi:10.1055/s-1987-27973

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Synthesis 1987; 1987(5): 471-474
DOI: 10.1055/s-1987-27973

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A Novel Synthesis of Bicyclic Isoxazolines via Sequential Michael and Intramolecular 1,3-Dipolar Additions

Hidemitsu Uno^* , Noriko Watanabe, Satomi Fujiki, Hitomi Suzuki

^*Advanced Instrumentation Center for Chemical Analysis, Ehime University, Bunkyo-cho 2-5, Matsuyama 790, Japan

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Publikationsdatum:
18. September 2002 (online)

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Bicyclic isoxazolines are obtained in good yields by the titanium tetrachloride-mediated reaction of allylic stannanes with 1-nitroalkadienes. Titanium tetrachloride converts stannyl nitronates generated in the Michael addition step to nitrile oxide equivalents which, on adding triethylamine, undergo intramolecular 1,3-dipolar cycloaddition to give the isoxazolines.