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Title: Diastereoselective Weitz-Scheffer epoxidation of levoglucosenone for the synthesis of isolevoglucosenone and derivatives
Contributor(s): Ledingham, Edward T  (author); Greatrex, Ben W  (author)orcid 
Publication Date: 2018-10-18
Early Online Version: 2018-08-25
DOI: 10.1016/j.tet.2018.08.041
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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.
Publication Type: Journal Article
Source of Publication: Tetrahedron, 74(42), p. 6107-6115
Publisher: Pergamon Press
Place of Publication: United Kingdom
ISSN: 0040-4020
Field of Research (FOR): 030503 Organic Chemical Synthesis
030504 Organic Green Chemistry
Socio-Economic Outcome Codes: 970103 Expanding Knowledge in the Chemical Sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
Appears in Collections:Journal Article
School of Rural Medicine
School of Science and Technology

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