Organocatalytic enantioselective aminosulfenylation of α,β- unsaturated aldehydes

Gui Ling Zhao, Ramon Rios, Jan Vesely, Lars Eriksson, Armando Córdova

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123 Scopus citations

Abstract

(Chemical Equation Presented) Domino theory: A simple, highly enantioselective organocatalytic aminosulfenylation of α,β- unsaturated aldehydes affords orthogonally protected β-amino-α- mercaptoaldehydes in high yields and 93 to >99% ee (see scheme, Bn=benzyl). Notably, the catalytic transformation shows that it is possible to efficiently employ all components of an electrophile, which includes a nucleofuge, in organocatalytic domino reactions of enals.

Original languageBritish English
Pages (from-to)8468-8472
Number of pages5
JournalAngewandte Chemie - International Edition
Volume47
Issue number44
DOIs
StatePublished - 20 Oct 2008

Keywords

  • Aldehydes
  • Asymmetric catalysis
  • Domino reactions
  • Nucleophilic substitution
  • Organocatalysis

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