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Preparation of diastereomerically pure dilignol model compounds
Julien Buendia1, Jakob Mottweiler, Carsten Bolm
1Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen, Germany.
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.
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