Synfacts 2007(9): 0983-0983  
DOI: 10.1055/s-2007-968882
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Peptide-Catalyzed Asymmetric Epoxidation

Contributor(s): Benjamin List, Daniela Kampen
G. Peris, C. E. Jakobsche, S. J. Miller*
Yale University, New Haven, USA
Further Information

Publication History

Publication Date:
23 August 2007 (online)


Peptide 1 has been designed as organocatalyst for an asymmetric epoxidation of alkenes 2. Protected allylic alcohols 2 react with aqueous H2O2 in the presence of chiral aspartate 1 (10 mol%), DIC, and DMAP to give epoxides 3 in good yields and enantioselectivities. Both cyclic and acyclic precursors can be used. The underlying catalytic cycle presumably involves peracid 4 generated in situ from acid 1 through carboxyl activation.