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Oxa-Michael-initiated cascade reactions of levoglucosenone.

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.

SUBMITTER: Klepp J

PROVIDER: S-EPMC9577383 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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Oxa-Michael-initiated cascade reactions of levoglucosenone.

Klepp Julian J Bousfield Thomas T Cummins Hugh H Legendre Sarah V A-M SVA Camp Jason E JE Greatrex Ben W BW

Beilstein journal of organic chemistry 20221013

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 ...[more]

PMID: 36300013

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