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Synthesis 1987; 1987(1): 77-79
DOI: 10.1055/s-1987-27856
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Efficient Synthesis of 6-Trimethylsiloxy- and 6-(Trimethylsilyl)-methyl-3-phenyl-5, 6,dihydro-4H-1,2-oxazines by Cycloaddition of α-Nitrosostyrene to Silyl Enol Ethers and Allyltrimethylsilane

Claudia Hippeli* , Hans-Ulrich Reissig
  • *Institut für Organische Chemie der Universität, Am Hubland, D-8700 Würzburg, West Germany
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Publikationsdatum:
20. August 2002 (online)

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The title compounds 3 are prepared in good yield from silyl enol ethers 1 and α-nitrosostyrene 2, generated in situ from α-chloroacetophenone oxime 4. Allyltrimethylsilane smoothly affords cycloadduct 5 which could be opened to the unsaturated ketone 6 or amino olefin 7.