title: Asymmetric dihydroxylations of enynes with a trisubstituted C═C bond. An unprecedented route to γ-lactone building blocks with a quaternary stereocenter.
abstract: En route to a comprehensive set of hydroxylactone building blocks (4R,5R)-, (4R,5S)-, (4S,5R)-, and (4S,5S)-5a, Sharpless asymmetric dihydroxylations of allylic chlorides (E)- and (Z)-9 were performed. They delivered the four stereoisomers of diol 10 with up to 92% ee and absolute configurations, which were proven to be in accordance with the Sharpless mnemonic.
authors.affiliation: Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität, Freiburg im Breisgau, Germany.
authors.forename: Heike
authors.initials: H
authors.lastname: Burghart-Stoll
authors.forename: Tobias
authors.initials: T
authors.lastname: Kapferer
authors.forename: Reinhard
authors.initials: R
authors.lastname: Brückner
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000475:Alkenes; D000480:Alkynes; D006843:Hydrocarbons, Chlorinated; D007783:Lactones