title: Enantiopure 1,4-diols and 1,4-aminoalcohols via stereoselective acyclic sulfoxide-sulfenate rearrangement.
abstract: Treatment of acyclic α-hydroxy and α-tosylamino sulfinyl dienes with amines affords enantiopure 1,4-diol or 1,4-hydroxysulfonamide derivatives in good yields and diastereoselectivities. This one-pot procedure entails a conjugate addition that triggers a diastereoselective sulfoxide-sulfenate [2,3]-sigmatropic rearrangement.
authors.affiliation: Instituto de Química Orgánica General, IQOG-CSIC. Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Roberto
authors.initials: R
authors.lastname: Fernández de la Pradilla
authors.forename: Ignacio
authors.initials: I
authors.lastname: Colomer
authors.forename: Mercedes
authors.initials: M
authors.lastname: Ureña
authors.forename: Alma
authors.initials: A
authors.lastname: Viso
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis*; D000586:Amination; D015394:Molecular Structure; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013434:Sulfenic Acids / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000438:Alcohols; D013434:Sulfenic Acids; D013454:Sulfoxides; D012451:Safrole; C005746:sulfoxide