Highly enantioselective addition of 1-fluoro-1-nitro(phenylsulfonyl)methane to α,β-unsaturated aldehydes

Martin Kamlar, Natalia Bravo, Andrea Nekane R. Alba, Simona Hybelbauerová, Ivana Císařová, Jan Veselý, Albert Moyano, Ramon Rios

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32 Scopus citations

Abstract

An organocatalytic, highly enantioselective addition of 1fluoro-1-nitro(phenylsulfonyl)methane to α,β-unsaturated aldehydes is reported. The reaction is simply catalyzed by secondary amines and furnishes the corresponding fluorinated derivatives in good yields, with moderate diastereoselectivities and excellent enantioselectivities. The absolute configuration of the major diastereomers was unambiguously ascertained by X-ray diffraction analysis.

Original languageBritish English
Pages (from-to)5464-5470
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number28
DOIs
StatePublished - Oct 2010

Keywords

  • Aldehydes
  • Diastereoselectivity
  • Enantioselectivity
  • Fluorine
  • Michael addition
  • Organocatalysis

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