title: Anti-Selective Aldol Reactions of Pentafluorosulfanylacetic Acid Esters with Aldehydes Mediated by Dicyclohexylchloroborane.
abstract: Aldol reactions of pentafluorosulfanyl (SF5)-substituted acetic acid esters with both aromatic and aliphatic aldehydes proceeded with excellent anti-diastereoselectivity and good to high yields using dicyclohexylchloroborane/triethylamine. This methodology enabled the synthesis of hitherto unknown α-SF5-β-hydroxy esters. Using a norephedrine-based auxiliary, high asymmetric induction was observed. The stereochemistry of products was assigned by NMR spectroscopy and proved by X-ray diffraction analysis. The intermediate enolate was identified as a highly unstable species.
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, D-48149 Münster, Germany.
authors.forename: Florian W
authors.initials: FW
authors.lastname: Friese
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, D-48149 Münster, Germany.
authors.forename: Anna-Lena
authors.initials: AL
authors.lastname: Dreier
authors.affiliation: Department of Chemistry, Advanced Materials Research Laboratory, Clemson University , 91 Technology Drive, Anderson, South Carolina 29625, United States.
authors.forename: Andrej V
authors.initials: AV
authors.lastname: Matsnev
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, D-48149 Münster, Germany.
authors.forename: Constantin G
authors.initials: CG
authors.lastname: Daniliuc
authors.affiliation: Department of Chemistry, Advanced Materials Research Laboratory, Clemson University , 91 Technology Drive, Anderson, South Carolina 29625, United States.
authors.forename: Joseph S
authors.initials: JS
authors.lastname: Thrasher
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, D-48149 Münster, Germany.|Cells-in-Motion Cluster of Excellence, Westfälische Wilhelms-Universität Münster , Waldeyerstraße 15, D-48149 Münster, Germany.
authors.forename: Günter
authors.initials: G
authors.lastname: Haufe