Synthesis of Trisubstituted Chromanes by Lewis-Base-Catalyzed Three-Component Electrophilic Thiofunctionalization of Cyclopropene with Phenols via a Formal [3 + 3] Annulation

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作者单位: Affiliations ¹ Faculty of Chemistry and Biology, Changchun University of Technology, 2055 Yan'an Street, Changchun, Jilin 130012, China. ² College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan, Shandong 250014, China. ³ School of Pharmacy, Shandong First Medical University & Shandong Academy of Medical Sciences, Tai-An, Shandong 271016, China.

摘要: A Lewis-base-catalyzed three-component electrophilic thiofunctionalization of cyclopropene with phenol is developed to furnish various trisubstituted chromanes in high trans-diasteroselectivity. This metal-free protocol is easy to scale-up, offers a unique 2,2,3-substitution pattern, and delivers chromanes with diversified core substitution patterns. The unprecedented tolerance of strong electron-withdrawing substituents at the phenol renders the protocol indispensable to access the otherwise in...更多; A Lewis-base-catalyzed three-component electrophilic thiofunctionalization of cyclopropene with phenol is developed to furnish various trisubstituted chromanes in high trans-diasteroselectivity. This metal-free protocol is easy to scale-up, offers a unique 2,2,3-substitution pattern, and delivers chromanes with diversified core substitution patterns. The unprecedented tolerance of strong electron-withdrawing substituents at the phenol renders the protocol indispensable to access the otherwise inaccessible chromane chemical space that is important for medicinal chemistry campaigns.收起

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