Laboratory for Advanced Materials and New Catalysis, School of Chemistry and Materials Science, Hubei University, Wuhan 430062, China,Laboratory of Natural Gas Utilization and Applied Catalysis, Dalian Institute of Chemical Physics of Chinese Academy of Sciences, Dalian 116023,China, and Jingmen Technological College, Jingmen 448000, ChinaReceived June 30, 2004

Advances in Homogeneous and Heterogeneous Catalytic Asymmetric Epoxidation

Charged intermediates and reagents are ubiquitous in organic transformations. The interaction of these ionic species with chiral neutral, anionic, or cationic small molecules has emerged as a powerful strategy for catalytic, enantioselective synthesis. This review describes developments in the burgeoning field of asymmetric ion-pairing catalysis with an emphasis on the insights that have been gleaned into the structural and mechanistic features that contribute to high asymmetric induction.

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Asymmetric ion-pairing catalysis.

Asymmetric Organocatalytic Cyclization and Cycloaddition Reactions

Enantioselective amino acid synthesis by chiral phase-transfer catalysis.

The use of chiral nonracemic onium salts and crown ethers as effective phase-transfer catalysts have been studied intensively primarily for enantioselective carbon-carbon or carbon-heteroatom bond-forming reactions under mild biphasic conditions. An essential issue for optimal asymmetric catalysis is the rational design of catalysts for targeted reaction, which allows generation of a well-defined chiral ion pair that reacts with electrophiles in a highly efficient and stereoselective manner. This concept, together with the synthetic versatility of phase-transfer catalysis, provides a reliable and general strategy for the practical asymmetric synthesis of highly valuable organic compounds.

P. G. Wainwright

Papers

A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids — Application in the enantioselective synthesis of α-amino acids

Asymmetric phase-transfer mediated epoxidation of α,β-unsaturated ketones using catalysts derived from Cinchona alkaloids

Phase-transfer catalysed asymmetric epoxidation of enones using N-anthracenylmethyl-substituted Cinchona alkaloids

Studies on the enantioselective synthesis of α-amino acids via asymmetric phase-transfer catalysis

Structure–selectivity studies on catalysts for the phase-transfer catalysed asymmetric alkylation of glycine imine esters