title: Stereochemistry of 1,5-benzothiazepin-4-one S-oxide: insight into the stereogenic elements at the sulfur atom and axis.
abstract: Oxidation of 1,5-benzothiazepin-4-one (5-A) stereoselectively afforded the S-oxide 8I-A (aS,1S) in preference to the diastereomer 8II-A (aS,1R) affected by the remote stereogenic axis. All the enantiomers (8I-A/8I-B and 8II-A/8II-B) were separated and isolated, and the interconversion between 8I and 8II (equilibrium ratio ≈5:1) was unequivocally verified to be caused by the rotation around the axis.
authors.affiliation: Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Hidetsugu
authors.initials: H
authors.lastname: Tabata
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Yoneda
authors.forename: Tetsuta
authors.initials: T
authors.lastname: Oshitari
authors.forename: Hideyo
authors.initials: H
authors.lastname: Takahashi
authors.forename: Hideaki
authors.initials: H
authors.lastname: Natsugari
mesh_terms: D003499:Cyclic S-Oxides / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*; D013841:Thiazepines / Q000737:chemistry*
chemical_list: D003499:Cyclic S-Oxides; D013841:Thiazepines; D013455:Sulfur