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Preparation of Diastereomerically Pure Dilignol Model Compounds
Author(s) -
Buendia Julien,
Mottweiler Jakob,
Bolm Carsten
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101579
Subject(s) - diastereomer , chemistry , cleavage (geology) , organic chemistry , combinatorial chemistry , materials science , composite material , fracture (geology)
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.