A simple and effective soluble polymer-bound ligand for the asymmetric dihydroxylation of olefins: DHQD-PHAL-OPEG-OMe

✍ Scribed by Yong-Qing Kuang; Sheng-Yong Zhang; Ling-Ling Wei

• Book ID: 104231166
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 69 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01105-4

✦ Synopsis

The synthesis of a novel soluble polymer-bound ligand DHQD-PHAL-OPEG-OMe and its application in the catalytic asymmetric dihydroxylation (AD) reaction are described. 1,4-Dichlorophthalazine was used as the coupling reagent to connect dihydroquinidine and polyethylene glycol monomethyl ether (MW=5000, Fluka) while providing an aromatic group at the 9-O-position of dihydroquinidine. Enantiomeric excesses for trans-disubstituted olefins in the AD reaction, with K 3 Fe(CN) 6 as secondary oxidant, are up to 98%.