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Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling.

Raphael K KlakeMytia D EdwardsJoshua D Sieber
Published in: Organic letters (2021)
Herein, we report the development of a catalytic enantioselective addition of N-substituted allyl equivalents to ketone electrophiles through use of Cu-catalyzed reductive coupling to access important chiral 1,2-aminoalcohol synthons in high levels of regio-, diastereo-, and enantioselectivity. Factors affecting enantioinduction are discussed including the identification of a reversible ketone allylation step that has not been previously reported in Cu-catalyzed reductive coupling.
Keyphrases
  • room temperature
  • ionic liquid
  • aqueous solution
  • metal organic framework
  • molecular docking
  • mass spectrometry