Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins

Hongmei Qin; Qimei Xie; Long He

doi:10.1039/d2ra03031d

Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins

RSC Adv. 2022 Jun 6;12(26):16684-16687. doi: 10.1039/d2ra03031d. eCollection 2022 Jun 1.

Authors

Hongmei Qin¹, Qimei Xie², Long He^{1

2}

Affiliations

¹ College of Chemistry and Materials Engineering, Guiyang University Guiyang 550005 P. R. China longhe@cwnu.edu.cn.
² College of Chemistry and Chemical Engineering, China West Normal University Nanchong 637002 P. R. China.

Abstract

A simple and convenient cyclization of ortho-hydroxyphenyl-substituted para-quinone methides with benzofuran-2-one type active olefins via oxa-Michael/1,6-conjugated addition has been developed, which afforded an easy access to enriched functionalized chroman-spirobenzofuran-2-one scaffolds with good to excellent yields (up to 90%) and diastereoselectivities (up to >19 : 1 dr). This reaction provided an efficient method for constructing desired spirocyclic compounds combining both well-known heterocyclic pharmacophores chroman and benzofuran-2-one.