Pure and Applied Chemistry
The Scientific Journal of IUPAC
Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen
12 Issues per year
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Biomimetic and organocatalytic approaches to oxidation catalysis
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.
Keywords: amino acids; asymmetric epoxidation; Biomimetic oxidation catalysis; C-C coupling; cyclopropanation; DIANANE; dynamic kinetic resolution; Nozaki-Hiyama-Kishi coupling; organocatalysis; Ru-porphyrins
International Conference on Organic Synthesis (ICOS-15), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 15th, Nagoya, Japan, 2004-08-01–2004-08-06
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