title: Catalytic Chemo-, E/Z-, and Enantioselective Cyclizations of o-Hydroxybenzyl Alcohols with Dimedone-Derived Enaminones.
abstract: A catalytic chemo-, E/Z-, and enantioselective cyclization of o-hydroxybenzyl alcohols with dimedone-derived enaminones has been established, which not only realized a chemoselective C1,2 cyclization of enaminones but also achieved the catalytic asymmetric construction of the biologically important tetrahydroxanthene framework with high E/Z- and enantioselectivities (all >95:5 E/Z, up to 98% yield, 97:3 er). This approach not only represents the first catalytic asymmetric C1,2 cyclization of enaminones with o-hydroxybenzyl alcohols but also provides an efficient strategy for constructing oxygenous heterocyclic frameworks with optical purity.
authors.affiliation: School of Chemistry & Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, People's Republic of China.
authors.forename: Jia-Jia
authors.initials: JJ
authors.lastname: Zhao
authors.affiliation: School of Chemistry & Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, People's Republic of China.
authors.forename: Yu-Chen
authors.initials: YC
authors.lastname: Zhang
authors.affiliation: School of Chemistry & Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, People's Republic of China.
authors.forename: Meng-Meng
authors.initials: MM
authors.lastname: Xu
authors.affiliation: School of Chemistry & Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, People's Republic of China.
authors.forename: Man
authors.initials: M
authors.lastname: Tang
authors.affiliation: School of Chemistry & Chemical Engineering and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou 221116, People's Republic of China.
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
mesh_terms: D001592:Benzyl Alcohols / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001592:Benzyl Alcohols; D003512:Cyclohexanones; D014966:Xanthenes; C004774:dimedone; C010631:salicyl alcohol