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Date of Award


Document Type

Thesis - Pacific Access Restricted

Degree Name

Master of Science (M.S.)



First Advisor

Paul H. Gross

First Committee Member

Xiaoling Li

Second Committee Member

Charles A. Matuszak

Third Committee Member

Michael J. Minch

Fourth Committee Member

Celestia Pryor


6-Chloronicotinic acid was coupled by an amide linkage to Merrifield resin or Jeffamine gel. Nucleophilic displacement of the 6-chloride group by hydroxide gave novel Merrifield resin catalyst 6 or Jeffamine gel catalyst 9 that were successfully used for Henry condensations. The condensation of 4,6-O-benzylidene-β-D-glucopyranose 11 with nitromethane gave 4,6-O-benzylidene-D-glucopyranosyl-l-nitromethane 12; the condensation of 11 with nitroethane gave α-R-(4,6-O-benzylidene-β-D-glucopyranosyl)-1-nitroethane 13 and its diastereomer 15; the condensation of 11 with nitropropane, followed by acetylation, gave α-R-(2,3-di-O-acetyl-4,6-O-benzylidene-β- D-glucopyranosyl)-1 -nitropropane 16 and its diastereomer 17; the condensation of 4,6- O-isopropylidene-β-D-glucopyranose 19 with nitromethane gave 4,6-O-isopropylidene- β-D-glucopyranosyl-1-nitromethane 20; the condensation of 4,6-O-isopropylidene-α- D-mannopyranose 21 with nitromethane gave 4,6-O-isopropylidene-β-D-mannopyranosyl- 1-nitromethane 23. These known compounds were obtained with improved yields compared to protocols with 1,3 proton transfer catalysts that were not bound to polymers. A new monomeric 1,3 proton transfer catalyst, 2,4 (1,3)-quinazolinedione 10, was also introduced.



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