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Tuning the enantioselective N-acetylation of racemic amines: A spectacular salt effect

Academic Article
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Overview

authors

  • Arseniyadis, S.
  • Subhash, P. V.
  • Valleix, A.
  • Mathew, S. P.
  • Blackmond, Donna
  • Wagner, A.
  • Mioskowski, C.

publication date

  • 2005

journal

  • Journal of the American Chemical Society  Journal

abstract

  • We have described a spectacular salt effect in the kinetic resolution of (+/-)-1-phenylethylamine, which leads to an increase in reactivity, high levels of selectivity, and a complete reversal of the stereoselectivity. By tuning the reaction conditions, we were able to increase the selectivity factor of (1S,2S)-1 to s = 115.
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja051302+

PubMed ID

  • 15853296
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Additional Document Info

start page

  • 6138

end page

  • 6139

volume

  • 127

issue

  • 17

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