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Peptide-Catalyzed Asymmetric Epoxidation
G. Peris, C. E. Jakobsche, S. J. Miller*
Yale University, New Haven, USA
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.