Synfacts 2014; 10(1): 0099
DOI: 10.1055/s-0033-1340383
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Cyclopropanation of α,β-Unsaturated Aldehydes with a Supported Peptide

Contributor(s):
Yasuhiro Uozumi
,
Fumie Sakurai
Akagawa K, Takigawa S, Nagamine IS, Umezawa R, Kudo K * University of Tokyo, Japan
Peptide-Catalyzed Diastereo- and Enantioselective Cyclopropanation of Aromatic α,β-Unsaturated Aldehydes.

Org. Lett. 2013;
15: 4964-4967
Further Information

Publication History

Publication Date:
13 December 2013 (online)

 

Significance

The amphiphilic resin-supported peptide 1 catalyzed the diastereo- and enantioselective cyclopropanation of aromatic α,β-unsaturated aldehydes 2 with dimethylphenacylsulfonium bromide in the presence of NaHCO3 to give the corresponding cyclopropanes 3 in 83–88% yield with 98–99% ee and 92–97% diastereoselectivity (9 examples, eq. 1). In the formation of 3g, the catalyst was recovered by filtration and reused five times without significant loss of its catalytic performance (1st reuse: 87% yield, 99% ee, 94% diastereoselectivity; 5th reuse: 83% yield, 99% ee, 95% diastereoselectivity).


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Comment

The authors have previously reported the preparation of a series of amphiphilic resin-supported peptides and their application to asymmetric hydrogenation (Org. Lett. 2008, 10, 2035), asymmetric Friedel–Crafts-type alkylation (Adv. Synth. Catal. 2012, 354, 1280) and asymmetric Michael addition (Angew. Chem. Int. Ed. 2012, 51, 12786).


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