A new practical method for the osmium-catalyzed dihydroxylation of olefins using bleach as the terminal oxidant

A general procedure for the osmium-catalyzed dihydroxylation of various olefins using bleach as oxidant is reported for the first time. Aromatic and aliphatic olefins yield the corresponding cis-1,2-diols in the presence of dihydroquinine or dihydroquinidine derivatives (Sharpless ligands) with good...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) no. 2; pp. 295 - 301
Main Authors Mehltretter, GM, Bhor, S, Klawonn, M, Dobler, C, Sundermeier, U, Eckert, M, Militzer, HC, Beller, M
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.01.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
homogenous catalysis
ALCOHOL DERIVATIVES
osmium
AIR
asymmetric catalysis
H2O2
SHARPLESS ASYMMETRIC DIHYDROXYLATION
LIGAND-ACCELERATED CATALYSIS
oxidations
ENANTIOSELECTIVE DIHYDROXYLATION
TETROXIDE
LEADS
dihydroxylation
Online AccessGet more information

Cover

More Information
Summary:A general procedure for the osmium-catalyzed dihydroxylation of various olefins using bleach as oxidant is reported for the first time. Aromatic and aliphatic olefins yield the corresponding cis-1,2-diols in the presence of dihydroquinine or dihydroquinidine derivatives (Sharpless ligands) with good to excellent chemo- and enantioselectivities under optimized pH conditions. In the presence of a small excess of bleach as reoxidant fast dihydroxylation takes place even at 0 degreesC. Under optimum reaction conditions it is possible to dihydroxylate terminal aliphatic and aromatic olefins as well as internal olefins. The low price of the oxidant and the simple handling of bleach make this dihydroxylation variant attractive for further applications.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2003-36826