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Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.

Makoto ShimizuMiki MushikaIsao MizotaYusong Zhu
Published in: RSC advances (2019)
Alkylation of iminomalonate with Grignard reagents followed by oxidation and allylation gave symmetrical quaternary α-amino diesters in good yields. Subsequent desymmetrization of a diol derivative from these products was conducted via asymmetric carbamylation catalyzed by Cu-Bnbox to give chiral quaternary aminodiol mono-carbamates.
Keyphrases
  • room temperature
  • hydrogen peroxide
  • ionic liquid
  • capillary electrophoresis
  • water soluble