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Author(s): Zaitsev AB; Adolfsson H
Title: Recent developments in asymmetric dihydroxylations
Source: SYNTHESIS-STUTTGART (11): 1725-1756
Date: 2006 JUN 1
Document Type: Journal : Review
DOI:
Language: English
Comment:
Address: Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden.
Reprint: Adolfsson, H, Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691
Stockholm, Sweden. E-mail: hansa@organ.su.se
Author Keywords: alkenes; asymmetric catalysis; dihydroxylations; diols; ligands; osmium
KeyWords Plus: OSMIUM-CATALYZED DIHYDROXYLATION; CINCHONA ALKALOID LIGAND; ALLYLIC
ALCOHOL SYSTEMS; CHIRAL FERROCENE DERIVATIVES; PROVIDE ADDITIONAL
EVIDENCE; POLYMER-BOUND LIGAND; VICINAL CIS-DIOLS; C,C DOUBLE-BONDS;
AD-MIX REAGENTS; ENANTIOSELECTIVE DIHYDROXYLATION
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.
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