Bulletin of the Korean Chemical Society

  • 제20권3호
  • /
  • Pages.325-328
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  • 1999
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Diastereoselectivity in the Reaction of 2-Piperidineacetates

  • 발행 : 1999.03.20
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초록

In the reactions of the enolates of various 2-piperidineacetates with iodomethane or trisyl azide, the anti isomer was always predominant over the syn one, independent of the stereochemistry of the piperidineacetates. The piperidineacetates having OTBDMS moiety at C5 proceeded more diastereoselectively than the compounds without the substituent. The diastereoselectivity could be explained by perpendicular model for the electrophilic substitution reaction.

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