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Keywords:

  • Amino ketones;
  • Amino alcohols;
  • Chiral sulfoxides;
  • Epoxidation;
  • Kinetic resolution;
  • Template synthesis;
  • Chirality

Abstract

A novel and efficient synthesis of enantiomerically pure α-dibenzylamino α′-sulfinyl ketones starting from a mixture of both epimers of α-bromo α′-(R)-sulfinyl ketone has been realized through combined in situ substitution–epimerization in a so-called Dynamic Kinetic Resolution (DKR). The scope of the reaction has been examined, and four differently substituted α-(S)-dibenzylamino α′-(R)-sulfinyl ketones were obtained in good yields with excellent diastereoselectivities. The utility of these derivatives was further illustrated with a highly stereoselective synthesis of syn-(2R,1′S)-2-(1-dibenzylaminoalkyl)oxiranes.