Asymmetric Nucleophilic Monofluorobenzylation of Allyl and Propargyl Halides Mediated by a Remote Sulfinyl Group: Synthesis of Homoallylic and Homopropargylic Fluorides

Asymmetric Nucleophilic Monofluorobenzylation of Allyl and Propargyl Halides Mediated by a Remote Sulfinyl Group: Synthesis of Homoallylic and Homopropargylic Fluorides

Fluorinated 2-(p-tolylsulfinyl)benzyl carbanions react with allyl and propargyl halides in a highly stereoselective way, providing homoallylic and homopropargylic fluorides, respectively, with high optical purity. Theoretical calculations found transition states for these transformations whose relat...

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Veröffentlicht in:Journal of organic chemistry 2014-08, Vol.79 (15), p.6970-6977
Hauptverfasser: Arroyo, Yolanda, Sanz-Tejedor, M. Ascensión, Parra, Alejandro, Alonso, Inés, García Ruano, José Luis
Format: Artikel
Sprache:eng
Schlagworte:
Anions - chemistry
Benzyl Compounds - chemistry
Fluorides - chemistry
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Pargyline - analogs & derivatives
Pargyline - chemical synthesis
Pargyline - chemistry
Quantum Theory
Stereoisomerism
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Zusammenfassung:Fluorinated 2-(p-tolylsulfinyl)benzyl carbanions react with allyl and propargyl halides in a highly stereoselective way, providing homoallylic and homopropargylic fluorides, respectively, with high optical purity. Theoretical calculations found transition states for these transformations whose relative stabilities are consistent with the experimentally observed stereoselectivity.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo501096f