Phosphine-Catalyzed Synthesis of 3-Allyl-4-pyrones by the Tandem Reaction of Diynones and Allylic Alcohols.

J Org Chem

Institute of Functional Organic Molecular Engineering, Henan Engineering Laboratory of Flame-Retardant and Functional Materials, College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004, China.

Published: November 2021

A simple and effective tandem reaction of diynones and allylic alcohols was developed to afford functionalized 3-allyl-4-pyrones in moderate to excellent yields. This protocol underwent a Michael addition─Claisen rearrangement─O-cyclization process, which exhibited broad substrate tolerance, high regioselectivity, and atom economy under a metal-free condition. Moreover, functional transformation of the products was also further studied.

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http://dx.doi.org/10.1021/acs.joc.1c01340DOI Listing

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