title: Enantioselective syntheses of spiroketals via a tandem reaction of Cu(I)-catalyzed cycloetherification and hydrogen-bond-induced [4 + 2] cyclization.
abstract: A tandem reaction consisting of a copper(I)-catalyzed cycloetherification and a hydrogen-bond-induced inverse-electron-demand oxa-Diels-Alder cycloaddition was performed from chiral propargyl alcohol, generating several kinds of optically pure [5, 6] spiroketals in excellent stereoselectivities and yields. The investigation on mechanism found that the cyclization prompted by a hydrogen bond not only improved the efficiency but also determined the diastereoselectivity.
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu P. R. China.
authors: Tian
authors: T
authors: Tian
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu P. R. China.
authors: Liqi
authors: L
authors: Li
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu P. R. China.
authors: Jijun
authors: J
authors: Xue
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu P. R. China.
authors: Jie
authors: J
authors: Zhang
authors: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu P. R. China.
authors: Ying
authors: Y
authors: Li
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D061565:Cycloaddition Reaction; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D004988:Ethers, Cyclic; D005663:Furans; D013141:Spiro Compounds; C520774:spiroketal; D003300:Copper