Efficient asymmetric α-oxyamination of aldehydes by resin-supported peptide catalyst in aqueous media

Kengo Akagawa; Takuma Fujiwara; Seiji Sakamoto; Kazuaki Kudo

doi:10.1021/ol100415h

Efficient asymmetric α-oxyamination of aldehydes by resin-supported peptide catalyst in aqueous media

Kengo Akagawa, Takuma Fujiwara, Seiji Sakamoto, Kazuaki Kudo

Division of Organic- and Biomaterials Research

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

70 Citations (Scopus)

Abstract

The resin-supported peptide catalyst having the terminal five-residue Pro-d-Pro-Aib-Trp-Trp combined with polyleucine successfully catalyzed the asymmetric α-oxyamination of aldehydes in aqueous media. The secondary structure and the chirality sense of the hydrophobic polyleucine chain significantly affected both reactivity and enantioselectivity.

Original language	English
Pages (from-to)	1804-1807
Number of pages	4
Journal	Organic letters
Volume	12
Issue number	8
DOIs	https://doi.org/10.1021/ol100415h
Publication status	Published - 2010 Apr 16

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol100415h

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title = "Efficient asymmetric α-oxyamination of aldehydes by resin-supported peptide catalyst in aqueous media",

abstract = "The resin-supported peptide catalyst having the terminal five-residue Pro-d-Pro-Aib-Trp-Trp combined with polyleucine successfully catalyzed the asymmetric α-oxyamination of aldehydes in aqueous media. The secondary structure and the chirality sense of the hydrophobic polyleucine chain significantly affected both reactivity and enantioselectivity.",

author = "Kengo Akagawa and Takuma Fujiwara and Seiji Sakamoto and Kazuaki Kudo",

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AU - Akagawa, Kengo

AU - Fujiwara, Takuma

AU - Sakamoto, Seiji

AU - Kudo, Kazuaki

PY - 2010/4/16

Y1 - 2010/4/16

N2 - The resin-supported peptide catalyst having the terminal five-residue Pro-d-Pro-Aib-Trp-Trp combined with polyleucine successfully catalyzed the asymmetric α-oxyamination of aldehydes in aqueous media. The secondary structure and the chirality sense of the hydrophobic polyleucine chain significantly affected both reactivity and enantioselectivity.

AB - The resin-supported peptide catalyst having the terminal five-residue Pro-d-Pro-Aib-Trp-Trp combined with polyleucine successfully catalyzed the asymmetric α-oxyamination of aldehydes in aqueous media. The secondary structure and the chirality sense of the hydrophobic polyleucine chain significantly affected both reactivity and enantioselectivity.

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Efficient asymmetric α-oxyamination of aldehydes by resin-supported peptide catalyst in aqueous media

Abstract

ASJC Scopus subject areas

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