title: Asymmetric synthesis of 1,3-dioxolanes by organocatalytic formal [3 + 2] cycloaddition via hemiacetal intermediates.
abstract: A novel asymmetric formal [3 + 2] cycloaddition reaction for the synthesis of 1,3-dioxolanes using cinchona-alkaloid-thiourea-based bifunctional organocatalysts is reported. The reaction proceeds via the formation of hemiacetal intermediates between γ-hydroxy-α,β-unsaturated ketones and aldehydes.
authors.affiliation: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan. keisuke.asano@t03kr913mk.mbox.media.kyoto-u.ac.jp
authors.forename: Keisuke
authors.initials: K
authors.lastname: Asano
authors.forename: Seijiro
authors.initials: S
authors.lastname: Matsubara
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013890:Thiourea / Q000737:chemistry
chemical_list: D000447:Aldehydes; D002930:Cinchona Alkaloids; D004148:Dioxolanes; D007659:Ketones; D013890:Thiourea