Peptide-catalyzed consecutive 1,6- and 1,4-additions of thiols to α,β,γ,δ-unsaturated aldehydes.
Regio- and enantioselective addition of thiols to α,β,γ,δ-unsaturated aldehydes was performed with a resin-supported peptide catalyst. It was shown that a 1,4-adduct was generated mainly at the initial stage of the reaction, and this was eventually converted to a thermodynamically stable 1,6- and 1,4-diadduct through retro-addition/addition reactions.
Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan. kkudo@iis.u-tokyo.ac.jp.
Kengo
K
Akagawa
Nobuhiro
N
Nishi
Jun
J
Sen
Kazuaki
K
Kudo
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D010455:Peptides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013997:Time Factors
D000447:Aldehydes; D000588:Amines; D010455:Peptides; D013438:Sulfhydryl Compounds