Abstract
Ever since the early discoveries that highly oxidized transition-metal reagents are
able to react with olefins to form oxidized organic compounds, chemists have investigated
and developed novel methods for selective oxidations. The major breakthrough by Sharpless
in the 1980s in discovering the osmium-catalyzed asymmetric dihydroxylation (AD) of
olefins has inspired numerous researchers, and as a result this particular scientific
area is currently thoroughly investigated. Nevertheless, new developments of this
highly useful reaction are still being made. The intent of this review is to highlight
recent developments achieved in asymmetric dihydroxylations with regards to improvement
of the catalytic systems and extension of the substrate scope.
1 Introduction
2 Mechanistic Considerations
3 Modifications
3.1 Ligand Development
3.2 Immobilized Catalysts
3.3 Oxidants in the AD Reaction
4 Substrate Scope of the AD Reaction
4.1 Empirical Rules for Predicting Facial Selectivity - The Mnemonic Device
4.2 New Substrates
5 AD on Substrates Containing Stereogenic Centers
5.1 Double Diastereoselection
5.2 Directed Dihydroxylation
5.3 Kinetic Resolution
5.4 Enantiomeric Enhancement by Dual AD
6 Miscellaneous Dihydroxylation Reactions and Systems
7 Concluding Remarks
Key words
alkenes - asymmetric catalysis - dihydroxylations - diols - ligands - osmium
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