Organocatalytic asymmetric transfer hydrogenation in aqueous media using resin-supported peptide having a polyleucine tether.
A resin-supported N-terminal prolyl peptide having a beta-turn motif and hydrophobic polyleucine chain effectively catalyzed the asymmetric transfer hydrogenation under aqueous conditions. The polyleucine tether provides a hydrophobic cavity in aqueous media that brought about a remarkable acceleration of the reaction. In addition, the polyleucine chain also turned out to be essential for high enantioselectivity.
Akagawa
Kengo
K
Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan.
Akabane
Hajime
H
Sakamoto
Seiji
S
Kudo
Kazuaki
K
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006865:Hydrogenation; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D012117:Resins, Synthetic / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000447:Aldehydes; D010455:Peptides; D012117:Resins, Synthetic; D014867:Water; C027819:polyleucine