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Polymeric cinchona alkaloids for the catalytic asymmetric dihydroxylation of olefins
Author(s) -
Cha Ruitao,
Wang Shaoyu,
Cheng Shaoling
Publication year - 2008
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.27710
Subject(s) - dihydroxylation , cinchona , copolymer , catalysis , chemistry , enantiomer , enantioselective synthesis , cinchona alkaloids , substrate (aquarium) , hydroxylation , organic chemistry , alkaloid , polymer chemistry , polymer , oceanography , geology , enzyme
Three cinchona alkaloid copolymers (PMMA‐BQTP, PMA‐BQTP, PAN‐BQTP) have been synthesized by copolymerization. Their structure was characterized by FTIR, GPC, and element analysis. The catalytic activity of these copolymers in asymmetric dihydroxylation (AD) of olefins by OsO 4 was studied. The products enantiomeric excesses (ee) and the conversion of the substrate in the dihydroxylation reactions were determined using HPLC. The effect of time, temperature, and recycle times on the reaction was also discussed. The results showed that the copolymers catalyzed the dihydroxylation of the olefins to get diols in high optical yield. However, their catalytic efficiency was largely depended on the nature of olefins. The polymeric cinchona alkaloid can be simply recovered at the end of the reaction by centrifugation and then reused without radical change of activity or enantioselectivity. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008