Asymmetric Michael addition of boronic acids to a γ-hydroxy-α,β-unsaturated aldehyde catalyzed by resin-supported peptide.
A resin-supported peptide catalyst effective for the asymmetric Michael addition of boronic acids to (E)-4-hydroxybut-2-enal was developed. From a spectral study, it was revealed that the optimum peptide consisted of both a β-turn and helix. Such a combination of secondary structures was essential for achieving a high catalytic ability.
Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan.
Kengo
K
Akagawa
Masahide
M
Sugiyama
Kazuaki
K
Kudo
D000447:Aldehydes / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D006900:Hydroxylation; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D001897:Boronic Acids; D010455:Peptides