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Synfacts 2010(7): 0839-0839  
DOI: 10.1055/s-0029-1220098
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Supported Peptide for Asymmetric α-Oxyamination of Aldehydes

Contributor(s):Yasuhiro Uozumi, Haifeng Zhou
K. Akagawa, T. Fujiwara, S. Sakamoto, K. Kudo*
The University of Tokyo, Japan
Efficient Asymmetric α-Oxyamination of Aldehydes by Resin-Supported Peptide Catalyst in Aqueous Media
Org. Lett.  2010,  12:  1804-1807  
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Publication History

Publication Date:
22 June 2010 (online)

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Key words

asymmetric α-oxyamination - peptide catalysis - aqueous media

Significance

A polystyrene-poly(ethylene glycol) resin supported peptide catalyst bearing terminal five-residue Pro-d-Pro-Aib-Trp-Trp combined with polyleucine was prepared. The polymeric peptide was successfully applied to the asymmetric α-oxyamination of aldehydes with TEMPO in the presence of a catalytic amount of FeCl2 and NaNO2 to give the corresponding products under aqueous aerobic conditions with up to 87% yield and 93% ee (5 examples).

Comment

The Kudo group has previously ­reported asymmetric hydrogenation (K. Akagawa et al. Tetrahedron: Asymmetry 2009, 20, 461; K. ­Akagawa et al. Org. Lett. 2008, 10, 2035) and asymmetric Friedel-Crafts alkylation (K. Akagawa et al. Tetrahedron Lett. 2009, 50, 5602) in aqueous media with this catalyst. The polyleucine moiety between the tryptophan and the resin support not only provides a hydrophobic environment, but also effects the stereoselectivity of the reaction.

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