title: Remote stereocontrol in the synthesis of acyclic 1,4-diols and 1,4-aminoalcohols from 2-sulfinyl dienes.
abstract: The highly diastereoselective conjugate addition of alcohols and amines (RXH) to enantiopure 2-sulfinyl dienes renders transient allylic sulfoxides which undergo sulfoxide-sulfenate rearrangement and sulfenate cleavage providing 2-ene-1,4-diols and 2-ene-1,4-aminoalcohols with up to 99:1 dr. The method allows for the generation of two stereocenters in a single synthetic operation with remote chirality transfer of one center into the other.
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: Marina
authors.initials: M
authors.lastname: Velado
authors.forename: Ignacio
authors.initials: I
authors.lastname: Colomer
authors.forename: Carmen
authors.initials: C
authors.lastname: Simal
authors.forename: Alma
authors.initials: A
authors.lastname: Viso
authors.forename: Heinz
authors.initials: H
authors.lastname: Gornitzka
authors.forename: Catherine
authors.initials: C
authors.lastname: Hemmert
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011090:Polyenes / Q000737:chemistry*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000588:Amines; D000605:Amino Alcohols; D011090:Polyenes; D013454:Sulfoxides