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.

Beilstein J. Org. Chem. 2022, 18, 1457–1462. doi:10.3762/bjoc.18.151

Source: Beilstein Journal of Organic Chemistry - October 13, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: cascade reactions green chemistry levoglucosenone oxa-Michael reaction Full Research Paper Source Type: research