Diastereoselective Weitz-Scheffer epoxidation of levoglucosenone for the synthesis of isolevoglucosenone and derivatives

Title
Diastereoselective Weitz-Scheffer epoxidation of levoglucosenone for the synthesis of isolevoglucosenone and derivatives
Publication Date
2018-10-18
Author(s)
Ledingham, Edward T
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
Elsevier Ltd
Place of publication
United Kingdom
DOI
10.1016/j.tet.2018.08.041
UNE publication id
une:1959.11/26734
Abstract
High-yielding epoxidation conditions for the cellulose pyrolysis product (−)-levoglucosenone (LGO) and 3-aryl derivatives of LGO have been developed. The reaction of LGO with hydrogen peroxide/base is known to give a Baeyer-Villiger reaction, however, it was found that the reactions of LGO or derivatives with tert-butylhydroperoxide/base affords solely epoxides through the Weitz-Scheffer reaction. A critical parameter in the successful isolation of the epoxide from LGO was to avoid all contact with water or alcohols during the reaction and workup. The epoxide products were reacted under Wharton conditions affording allylic alcohols and subsequent oxidation led to isolevoglucosenone or 3-arylisolevoglucosenone derivatives. Previously unreported reactions on isolevoglucosenone were then investigated.
Link
Citation
Tetrahedron, 74(42), p. 6107-6115
ISSN
1464-5416
0040-4020
Start page
6107
End page
6115

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