title: Synthesis of enantiomerically pure lignin dimer models for catalytic selectivity studies.
abstract: A series of highly enantioselective transformations, such as the Sharpless asymmetric epoxidation and Jacobsen hydrolytic kinetic resolution, were utilized to achieve the complete stereoselective synthesis of β-O-4 lignin dimer models containing the S, G, and H subunits with excellent ee (>99%) and moderate to high yields. This unprecedented synthetic method can be exploited for enzymatic, microbial, and chemical investigations into lignin's degradation and depolymerization as related to its stereochemical constitution. Preliminary degradation studies using enantiopure Co(salen) catalysts are also reported.
authors.affiliation: Department of Chemistry, University of Tennessee , Knoxville, Tennessee 37996, United States.
authors.forename: Costyl N
authors.initials: CN
authors.lastname: Njiojob
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Rhinehart
authors.forename: Joseph J
authors.initials: JJ
authors.lastname: Bozell
authors.forename: Brian K
authors.initials: BK
authors.lastname: Long
mesh_terms: D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry*; D007700:Kinetics; D008031:Lignin / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D005029:Ethylenediamines; D003035:Cobalt; D008031:Lignin; C011452:disalicylaldehyde ethylenediamine