Asymmetric transfer hydrogenation in aqueous media catalyzed by resin-supported peptide having a polyleucine tether

Kengo Akagawa; Hajime Akabane; Seiji Sakamoto; Kazuaki Kudo

doi:10.1016/j.tetasy.2009.02.036

Asymmetric transfer hydrogenation in aqueous media catalyzed by resin-supported peptide having a polyleucine tether

Kengo Akagawa, Hajime Akabane, Seiji Sakamoto, Kazuaki Kudo

Division of Organic- and Biomaterials Research

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

Abstract

A resin-supported N-terminal prolyl peptide having a β-turn motif and a polyleucine tether has been developed for the organocatalytic asymmetric transfer hydrogenation under aqueous conditions. Polyleucine accelerated the reaction in a highly enantioselective manner by providing a hydrophobic microenvironment around the prolyl residue. The investigation of catalyst structures indicates that the l-form of polyleucine is essential for both reaction efficiency and enantioselectivity.

Original language	English
Pages (from-to)	461-466
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	20
Issue number	4
DOIs	https://doi.org/10.1016/j.tetasy.2009.02.036
Publication status	Published - 2009 Mar 11

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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AU - Sakamoto, Seiji

AU - Kudo, Kazuaki

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AB - A resin-supported N-terminal prolyl peptide having a β-turn motif and a polyleucine tether has been developed for the organocatalytic asymmetric transfer hydrogenation under aqueous conditions. Polyleucine accelerated the reaction in a highly enantioselective manner by providing a hydrophobic microenvironment around the prolyl residue. The investigation of catalyst structures indicates that the l-form of polyleucine is essential for both reaction efficiency and enantioselectivity.

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