Biomimetic and organocatalytic approaches to oxidation catalysis

Abstract

The lecture summarized our recent work in the fields of (i) catalytic asymmetric epoxidation and cyclopropanation, (ii) C-C coupling reactions, and (iii) dynamic kinetic resolution (DKR). The first section describes the use of chiral Ru-porphyrins as catalysts for the asymmetric epoxidation and cyclopropanation of nonfunctionalized olefins, and of peptides and alkaloid-based phase-transfer catalysts for the asymmetric epoxidation of enones. The second section highlights the application of the DIANANE-salen ligands (DIANANE: endo, endo-2,5-diamino-norbornane) to the asymmetric Nozaki-Hiyama-Kishi coupling of aldehydes with allylic and vinylic electrophiles, and of N-tosyl proline amides for asymmetric aldol additions. In the final section, bifunctional urea-based organocatalysts for the DKR of azlactones to provide enantiomerically enriched amino acid esters are presented. © 2005 IUPAC.