Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone

Xinghua Ma; Xin Liu; Patrick Yates; Warwick Raverty; Martin G. Banwell; Chenxi Ma; Anthony C. Willis; Paul D. Carr

doi:10.1016/j.tet.2018.03.023

Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone

Xinghua Ma, Xin Liu, Patrick Yates, Warwick Raverty, Martin G. Banwell^*, Chenxi Ma, Anthony C. Willis, Paul D. Carr

^*Corresponding author for this work

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15 Citations (Scopus)

Abstract

The manipulation of the enone moiety associated with the biomass-derived, homochiral and now abundant compound levoglucosenone (1) is described. While the trichloroacetimidates derived from the allylic alcohols 3 and 4 failed to engage in Overman-type rearrangements, certain ester derivatives reacted in the presence of Pd[0]-catalysts to give regio-isomeric mixtures of β,γ-unsaturated malonates or ketones, the structures of which were confirmed by single-crystal X-ray analyses. In other sequences involving 1,3-transposition reactions, an operationally simple means for converting compound 1 into isolevoglucosenone (2) is described.[Figure

Original language	English
Pages (from-to)	5000-5011
Number of pages	12
Journal	Tetrahedron
Volume	74
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2018.03.023
Publication status	Published - 20 Sept 2018

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T2 - 1,3-Transposition reactions including ones leading to isolevoglucosenone

AU - Ma, Xinghua

AU - Liu, Xin

AU - Yates, Patrick

AU - Raverty, Warwick

AU - Banwell, Martin G.

AU - Ma, Chenxi

AU - Willis, Anthony C.

AU - Carr, Paul D.

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KW - 1,3-Transposition

KW - Isolevoglucosenone

KW - Levoglucoseone

KW - Tsuji-Trost reaction

KW - Unsaturated esters

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JO - Tetrahedron

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Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone

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