Oxa-Michael-initiated cascade reactions of levoglucosenone

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 th...

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Bibliographic Details
Published in:	Beilstein journal of organic chemistry Vol. 18; no. 1; pp. 1457 - 1462
Main Authors:	Klepp, Julian, Bousfield, Thomas, Cummins, Hugh, Legendre, Sarah V A-M, Camp, Jason E, Greatrex, Ben W
Format:	Journal Article
Language:	English
Published:	Frankfurt am Main Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 13-10-2022 Beilstein-Institut
Subjects:	Aldehydes cascade reactions Chemistry Equilibrium Full Research Paper green chemistry levoglucosenone oxa-michael reaction Temperature
Online Access:	Get full text
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Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1860-5397 2195-951X 1860-5397
DOI:	10.3762/bjoc.18.151