Enantioselective organocatalytic allylic amination.
A new strategy for catalytic enantioselective allylic amination based on organocatalysis has been developed. Using a commercially available organocatalyst we demonstrate a direct highly enantioselective allylic electrophilic functionalization of alkylidene cyanoacetates and malononitriles with azodicarboxylates. The reaction is broad in scope and proceeds in high yields and with enantioselectivities up to 99%. Furthermore, we demonstrate the synthetic utility of the optically active products formed: highly diastereoselective Diels-Alder reaction, reduction, and formation of optically active building blocks, which are found in various important bioactive compounds such as quinacrine, chloroquine, and analogues thereof.
Poulsen
Thomas B
TB
The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.
Alemparte
Carlos
C
Jørgensen
Karl Anker
KA
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D009942:Organometallic Compounds