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...

Full description

Saved in:
Bibliographic Details
Published in:Beilstein journal of organic chemistry 2022-10, Vol.18 (1), p.1457-1462
Main Authors: Klepp, Julian, Bousfield, Thomas, Cummins, Hugh, Legendre, Sarah V A-M, Camp, Jason E, Greatrex, Ben W
Format: Article
Language:English
Subjects:
Aldehydes
cascade reactions
Chemistry
Equilibrium
Full Research Paper
green chemistry
levoglucosenone
oxa-michael reaction
Temperature
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
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.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.18.151