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Synfacts 2009(11): 1298-1298  
DOI: 10.1055/s-0029-1218069
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Alkylation Using Resin-Supported Peptide Catalysts

Contributor(s): Yasuhiro Uozumi, Yoshikazu Yamamoto
K. Akagawa, T. Yamashita, S. Sakamoto, K. Kudo*
The University of Tokyo and Tohoku University, Sendai, Japan
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

The PS-PEG supported N-terminal prolyl peptide 1 bearing a polyleucine moiety promoted the Friedel-Crafts-type alkylation of indoles and pyrroles 3 with α,β-unsaturated aldehydes 2 in aqueous THF to give the corresponding products 4 in 56-85% yield with 52-88% ee (6 examples). Catalyst 1 was recovered by simple filtration and reused five times without loss of catalytic activity and stereoselectivity for the formation of 4a (1st-5th reuse; 70-76% yield, 88-90% ee).