4.5 Article

Asymmetric α-Allylation of α-Branched Aldehydes with Allyl Alcohols by Synergistic Catalysis Using an Achiral Palladium Complex and a Chiral Primary Amino Acid

Journal

SYNTHESIS-STUTTGART
Volume 46, Issue 10, Pages 1367-1373

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1340901

Keywords

aldehydes; allylation; amino acids; asymmetric catalysis; palladium

Funding

  1. MEXT, Japan (KAKENHI) [24105501]
  2. MEXT, Japan, program 'Strategic Molecular and Materials Chemistry through Innovative Coupling Reactions' of Hokkaido University
  3. Grants-in-Aid for Scientific Research [26105701, 24105501] Funding Source: KAKEN

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Highly enantioselective direct alpha-allylation of alpha-branched aldehydes with simple allyl alcohols was achieved by the combined use of an achiral transition-metal catalysis with a palladium complex and a chiral organocatalysis with a readily obtainable primary a-amino acid. Various alpha-allylated aldehydes possessing a stereo-controlled quaternary carbon stereogenic center were synthesized in high yields with high enantioselectivity.

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