title: From 2-aminomethyl-1,4-benzodioxane enantiomers to unichiral 2-cyano- and 2-carbonyl-substituted benzodioxanes via dichloroamine.
abstract: 2-Substituted 1,4-benzodioxanes, such as 2-cyano-, 2-methoxycarbonyl-, 2-aminocarbonyl-, and 2-formyl-1,4-benzodioxane, are key synthons that for the most part are never described as enantiomers or are inadequately characterized for enantiomeric purity. They were prepared by quantitative N,N-dichlorination of (R)- and (S)-2-aminomethyl-1,4-benzodioxane and successive functional group conversions in high yields without any racemization of the stereogenic benzodioxane C(2).
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Sezione "Pietro Pratesi", Università degli Studi di Milano , via Mangiagalli 25, I-20133 Milano, Italia.
authors.forename: Cristiano
authors.initials: C
authors.lastname: Bolchi
authors.forename: Ermanno
authors.initials: E
authors.lastname: Valoti
authors.forename: Valentina
authors.initials: V
authors.lastname: Straniero
authors.forename: Paola
authors.initials: P
authors.lastname: Ruggeri
authors.forename: Marco
authors.initials: M
authors.lastname: Pallavicini
mesh_terms: D002700:Chloramines / Q000737:chemistry*; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry; D008744:Methylamines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C000592996:2-aminomethyl-1,4-benzodioxane; D002700:Chloramines; D004146:Dioxanes; D008744:Methylamines