AI Article Synopsis
- * Initial experiments indicate that the first significant reaction step is a highly selective alkyne-carbonyl metathesis involving the 1,3-diynes and alkyl glyoxylates, aided by Lewis acid.
- * The final product formation involves further hydration and an oxa-Michael addition, facilitated by Brønsted acid, resulting in the creation of two C-O bonds in a five-membered oxygen-containing ring.
Article Abstract
The cooperative Lewis and Brønsted acid catalysis makes convergent synthesis of 3(2H)-furanones through a three-component coupling of 1,3-diynes, alkyl glyoxylates and water. Control experiments support that Lewis acid-catalyzed highly chemo-, regio- and stereoselective alkyne-carbonyl metathesis of 1,3-diynes and alkyl glyoxylates might be the initial step of this multicomponent annulation. Further chemo- and regioselective hydration of the alkyne-carbonyl metathesis product and subsequent oxa-Michael addition promoted by Brønsted acid results in the formation of two C-O bonds of the five-membered oxygen heterocycle.
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| http://dx.doi.org/10.1002/chem.202401999 | DOI Listing |
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