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Oxa-Michael-initiated cascade reactions of levoglucosenone |
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Beilstein - Institut zur Foerderung der Chemischen Wissenschaften |
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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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Beilstein Journal of Organic Chemistry, v.18, p. 1457-1462 |
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Attribution 4.0 International |
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Attribution 4.0 International |
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