Highly stereoselective methylene transfers onto butanediacetal-protected chiral non-racemic sulfinyl imines using S-ylide technology

Chem Commun (Camb). 2009 Apr 14:(14):1882-4. doi: 10.1039/b822779a. Epub 2009 Mar 9.

Abstract

Diastereomeric ratios of >95 : 5 were obtained when performing methylene transfers onto imines originating from d-mannitol and (S)-(-)-2-methyl-2-propane sulfinamide or ascorbic acid and (R)-(-)-2-methyl-2-propane sulfinamide.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetoacetates / chemistry*
  • Amides / chemistry
  • Ascorbic Acid / chemistry
  • Imines / chemistry*
  • Mannitol / chemistry
  • Methane / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Acetoacetates
  • Amides
  • Imines
  • Mannitol
  • acetoacetic acid
  • Methane
  • Ascorbic Acid