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Keywords:

  • α-amido sulfones;
  • asymmetric synthesis;
  • aza-Henry reaction;
  • imines;
  • rosin-derived thiourea

Abstract

The doubly stereocontrolled organocatalytic aza-Henry reaction of nitroalkanes to N-Boc-imines generated in situ from a variety of substituted α-amido sulfones was investigated for the first time, in general, affording the corresponding products with high to excellent yields (up to 93% yield) and enantioselectivities (up to 98% ee), and satisfactory diastereoselectivies (anti/syn up to 98:2). Furthermore, these organocatalysts based on rosin have been proved to be the very effective promoters for this catalytic asymmetric process along side the Cinchona alkaloid-derived catalysts.