Recent Developments in Asymmetric Dihydroxylations

Alexey B. Zaitsev; Hans Adolfsson

doi:10.1055/s-2006-942378

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Synthesis 2006(11): 1725-1756
DOI: 10.1055/s-2006-942378

REVIEW

Recent Developments in Asymmetric Dihydroxylations

Alexey B. Zaitsev, Hans Adolfsson*
Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden
Fax: +46(8)154908; e-Mail: hansa@organ.su.se;

Further Information

Publication History

Received 14 October 2005
Publication Date:
05 May 2006 (online)

Abstract
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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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53

Adolfsson H., Stålfors F.; Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego CA, April 1-5, 2001; American Chemical Society: Washington DC, 2001; 616-ORGN.