title: Dehydrative reduction: a highly diastereoselective synthesis of syn-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane.
abstract: TFA/Et(3)SiH-mediated cyclization of thioketones 5 derived from the reaction of functionalized thiophenols (catechols) with bromo ketones gave syn 2,3-bisaryl(or heteroaryl) dihydrobenzoxathiins and benzodioxane 1 with total diastereoselectivity (>99:1), in excellent yields.
authors.affiliation: Department of Medicinal Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, USA. seongkon_kim@merck.com
authors.forename: Seongkon
authors.initials: S
authors.lastname: Kim
authors.forename: Jane Y
authors.initials: JY
authors.lastname: Wu
authors.forename: Helen Y
authors.initials: HY
authors.lastname: Chen
authors.forename: Frank
authors.initials: F
authors.lastname: DiNinno
mesh_terms: D002396:Catechols / Q000737:chemistry; D003500:Cyclization; D004146:Dioxanes / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D002396:Catechols; D004146:Dioxanes; D007659:Ketones