title: Preparation of diastereomerically pure dilignol model compounds.
abstract: A gram-scale synthetic access to diastereomerically pure dilignol β-O-4 type model compounds, which represent valuable candidates for studies of lignin cleavage and valorization, is described. Following a straightforward procedure both diastereoisomers of 1,3-dilignols can be prepared. In the key-step, tert-butyl aryloxy esters are used as enolate precursors for additions on aldehydes. After separation, the resulting erythro and threo β-hydroxy esters are independently reduced to afford the target compounds in high yields.
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen, Germany.
authors.forename: Julien
authors.initials: J
authors.lastname: Buendia
authors.forename: Jakob
authors.initials: J
authors.lastname: Mottweiler
authors.forename: Carsten
authors.initials: C
authors.lastname: Bolm
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters; D008031:Lignin / Q000031:analogs & derivatives* / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001555:Benzene Derivatives; D004952:Esters; D008031:Lignin