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2005
Enantioselective syntheses
O 0031
Polysiloxane-Bound Ligand Accelerated Catalysis: A Modular Approach to
and Homogeneous Macromolecular Asymmetric Dihydroxylation
04- 035 Heterogeneous
Ligands. — The development of a covalently polysiloxane-bound ligand for the
OsO4-catalyzed asymmetric dihydroxylation reaction is described. Best results are
achieved with a (DHQ)2-PHAL-analogous polymer-bound ligand (LIG). Additionally,
concomitant introduction of an alkoxy ethylester group into the polymer is used to adjust the solubility and, thereby, the reactivity of the ligand. Thus, the (DHQ)2-PHAL-analogous ligand is a heterogeneous catalyst while the related mixed ligand (cinchona
alkaloid/alkoxyethylester residue = 5:7) is fully soluble in the AD-mixture applied and
provides comparable results in shorter reaction times. — (DECLUE, M. S.; SIEGEL*,
J. S.; Org. Biomol. Chem. 2 (2004) 16, 2287-2298; Org.-Chem. Inst., Univ. Zuerich,
CH-8057 Zuerich, Switz.; Eng.) — Mischke
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