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Published on: August 14, 2019
Oxa-Michael-initiated cascade reactions of levoglucosenone
Julian Klepp1, Thomas Bousfield2, Hugh Cummins1
1School of Rural Medicine, University of New England, Armidale, NSW, 2351, Australia.
Abstract:
The reactions of aromatic aldehydes and levoglucosenone promoted by methoxide gives bridged α,β-unsaturated ketones, formed by a series of oxa-Michael-initiated cascade reactions in yields of up to 91% (14 examples). A complex series of equilibria operate during the reaction, and the formation of the bridged species is thermodynamically favored, except in the case of 5-methylfurfural and pyrrole-2-carboxaldehyde. This is the first report detailing this type of aldol/Michael cascade involving oxa-Michael initiation.
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