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Domino Michael/Mannich Annulation Reaction of N-Sulfinyl Lithiodienamines.

Xiao JinVijay K ChatarePo-Cheng YuMichael R GauOwen T O'SullivanRodrigo B Andrade
Published in: Organic letters (2021)
The domino Michael/Mannich (DMM) annulation reaction between an N-sulfinyl lithiodienamine and an electrophilic alkene is developed for the synthesis of chiral 2-amino cyclohexenes, a key building block in asymmetric synthesis. The DMM reaction proceeds at low temperature while maintaining the stereochemical fidelity. The product functionalized amino cyclohexenes, here obtained in 55-82% yield with diastereomeric ratios as high as >19:1.
Keyphrases
  • electron transfer
  • quantum dots
  • solid state
  • liquid chromatography