title: Synthesis of highly-substituted enantiomerically pure allylboronic esters and investigation of their stereoselective addition to aldehydes.
abstract: Diastereomerically pure allylboronates bearing the readily available tartrate derivative were obtained via sigmatropic rearrangement. Allyl additions were performed, and the influence of γ-disubstituted allylboronates was studied. Highly γ-substituted boronic esters were found to lead to the corresponding enantiomerically enriched homoallyl alcohols with exclusively E configuration; their synthesis and the mechanism of the reaction is proposed here.
authors.affiliation: Institut für Bioorganische Chemie der Heinrich-Heine Universität Düsseldorf im Forschungszentrum Jülich , Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany.
authors.forename: Roza
authors.initials: R
authors.lastname: Vahabi
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Frey
authors.forename: Jörg
authors.initials: J
authors.lastname: Pietruszka
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D001897:Boronic Acids; D004952:Esters