Synthesis of a Chiral Auxiliary Family from Levoglucosenone and Evaluation in the Diels–Alder Reaction

Title
Synthesis of a Chiral Auxiliary Family from Levoglucosenone and Evaluation in the Diels–Alder Reaction
Publication Date
2018
Author(s)
Klepp, Julian
Sumby, Christopher J
Greatrex, Ben W
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
Georg Thieme Verlag
Place of publication
Germany
DOI
10.1055/s-0037-1610148
UNE publication id
une:1959.11/26829
Abstract
A new family of chiral auxiliaries has been developed based on the lignocellulosic biomass pyrolysis product levoglucosenone. A promising single stereoisomer with an alcohol and π-stacking phenyl substituents was prepared in excellent yield in two steps from di­hydrolevoglucosenone without chromatography on >50 g scale. Acrylate esters prepared from the auxiliaries underwent diastereoselective Lewis acid promoted Diels–Alder reactions with cyclopentadiene (­endo/exo 98:2, endo d.r. up to 98:2), dimethylbutadiene (d.r. 93:7), and isoprene (d.r. > 98:2)
Link
Citation
Synlett, 29(11), p. 1441-1446
ISSN
1437-2096
0936-5214
Start page
1441
End page
1446

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