title: Asymmetric tandem Michael-aldol reactions between 3-cinnamoyloxazolidine-2-thiones and aldehydes.
abstract: Reactions between chiral 3-cinnamoyl-4-methyl-5-phenyl-1,3-oxazolidine-2-thiones and aromatic aldehydes in the presence of BF3Et2O diastereoselectively produced tricyclic compounds incorporating a bridgehead carbon bound to four heteroatoms in high yields. Four stereocenters were induced during the reaction. The tricyclic products were transformed into propane-1,3-diols bearing three consecutive stereocenters by acid hydrolysis, S-methylation, and reductive removal of the chiral auxiliary.
authors.affiliation: Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan.
authors.forename: Hironori
authors.initials: H
authors.lastname: Kinoshita
authors.forename: Takashi
authors.initials: T
authors.lastname: Osamura
authors.forename: Kazumi
authors.initials: K
authors.lastname: Mizuno
authors.forename: Sayaka
authors.initials: S
authors.lastname: Kinoshita
authors.forename: Tatsunori
authors.initials: T
authors.lastname: Iwamura
authors.forename: Shin-Ichi
authors.initials: S
authors.lastname: Watanabe
authors.forename: Tadashi
authors.initials: T
authors.lastname: Kataoka
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.forename: Genzoh
authors.initials: G
authors.lastname: Tanabe
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001671:Biochemistry / Q000379:methods*; D002934:Cinnamates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013871:Thiones / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D002934:Cinnamates; D013871:Thiones; C116609:3-hydroxybutanal